Method for preparation of cyano compounds of the 13th group with a lewis acid

ABSTRACT

The invention discloses a method for preparation of cyano compounds of the 13th group of the periodic table with 1, 2, 3 or 4 cyano residues, represented by formula (I): [Cat n+ ][Z 1 F 4-m (CN) m ) − ] n  by a reaction of [(Z 1 F 4 ) − ] with trimethylsilylcyanide in the presence of a Lewis acid and in the presence of the cation Cat n+ ; Cat 2+  is a cation, Z 1  is B, Al, Ga, In or Tl, m is 1, 2, 3 or 4 and n is 1, 2, 3 or 4.

RELATED APPLICATIONS

This application is the national stage entry of International PatentApplication No. PCT/EP2014/070233 having a filing date of Sep. 23, 2014,which claims the filing benefit of European Patent Application No.13192373.2, having a filing date of Nov. 11, 2013, European PatentApplication No. 13193107.3, having a filing date of Nov. 15, 2013, U.S.Provisional Application No. 61/904,748, having a filing date of Nov. 15,2013, European Patent Application No. 14155420.4, having a filing dateof Feb. 17, 2014, European Patent Application No. 14167175.0, having afiling date of May 6, 2014, European Patent Application No. 14169209.5,having a filing date of May 21, 2014, European Patent Application No.14177996.7, having a filing date of Jul. 22, 2014, European PatentApplication No. 14178322.5, having a filing date of Jul. 24, 2014,European Patent Application No. 14179786.0, having a filing date of Aug.5, 2014, and European Patent Application No. 14181021.8, having a filingdate of Aug. 14, 2014, all of which are incorporated herein by referencein their entirety.

DESCRIPTION

The invention discloses a method for preparation of cyano compounds ofthe 13th group of the periodic table with 1, 2, 3 or 4 cyano residues,represented by formula (I),[Cat^(n+)][(Z¹F_(4-m)(CN)_(m))⁻]_(n)  (I)by a reaction of [(Z¹F₄)⁻] with trimethylsilylcyanide in the presence ofa Lewis acid and in the presence of the cation Cat^(n+);Cat^(n+) is a cation, Z¹ is B, Al, Ga, In or Tl, m is 1, 2, 3 or 4 and nis 1, 2, 3 or 4.

BACKGROUND OF THE INVENTION

The term “ionic liquid” (IL) is usually used to refer to a salt which isliquid at temperatures below 100° C., in particular at room temperature.Such liquid salts typically comprise organic cations and organic orinorganic anions, and are described inter alia in P. Wasserscheid etal., Angew. Chem., 2000, 112, 3926-3945.

Ionic liquids have a series of interesting properties: Usually, they arethermally stable, relatively non-flammable and have a low vaporpressure. They show good solvability for numerous organic and inorganicsubstances. In addition, ionic liquids have interesting electrochemicalproperties, for example electrical conductivity which is oftenaccompanied by a high electrochemical stability.

These attributes give rise to many applications of ionic liquids: Theycan be used foremost as solvent in synthesis, as electrolyte, aslubricant and as hydraulic fluid. Moreover they serve as phase-transfercatalyst, as extraction medium, as heat-transfer medium, assurface-active substance, as plasticizer, as conductive salt, organicsalt or additive in electrochemical cells, as electrolyte, as componentin electrolyte formulations, wherein such electrolyte formulationcomprising an ionic liquid is preferably used in electrochemical and/oroptoelectronic device such as a photovoltaic cell, a light emittingdevice, an electrochromic or photo-electrochromic device, anelectrochemical sensor and/or biosensor, particularly preferred in a dyesensitized solar cell.

Therefore, there is a fundamental need for ionic liquids having avariety of properties which open up additional opportunities for theiruse.

An interesting family of ionic liquids contains tetravalent boronanions. Tetrafluoroborate containing ionic liquids were among the firstof this new generation of compounds and 1-ethyl-3-methylimidazoliumtetrafluoroborate ([EMIm][BF₄]) was prepared via metathesis of [EMIm]Iwith Ag[BF₄] in methanol as disclosed by J. S. Wilkes et al., J. Chem.Soc. Chem. Commun. 1990, 965.

E. Bernhardt, Z. Anorg. Allg. Chem. 2003, 629, 677-685, discloses thereaction of M[BF₄] (M=Li, K) with (CH₃)₃SiCN (TMSCN). The preparation ofLi[BF(CN)₃] is disclosed to take 7 days, that of K[BF(CN)₃] takes onemonth. The yield of K[BF(CN)₃] was 60%, the product contained 5%K[BF₂(CN)₂]. The molar ratio of [BF₄]⁻:TMSCN was 1:7.8.

US 2011/150736 A1 discloses as a “Third Production Method” a reaction ofthree compounds: TMSCN, an amine or ammonium salt, and a boron compound.

EP 2 327 707 A claims in claim 7 a method for producing an ioniccompound represented by the general formula (I), comprising a step ofreacting starting materials containing a cyanide and a boron compound.General formula (I) is a salt of a cation Kt^(m+) with [B(CN)₄]⁻.

The examples disclose various methods for preparing tetrabutylammoniumtetracyanoborate, for example:

-   1) Example 1-1 of EP 2 327 707 A discloses a reaction of    tetrabutylammonium bromide, zinc (II) cyanide and boron tribromide    in toluene at 130° C. for 2 days, with a yield of 35%. The molar    ratio of boron compound:TMSCN was 1:5.5.-   2) Example 2-1 of EP 2 327 707 A discloses a reaction of    tetrabutylammonium bromide, tetrabutylammonium cyanide and boron    tribromide in toluene at 130° C. for 2 days, with a yield of 77%.    The molar ratio of boron compound:tetrabutylammonium cyanide was    1:7.1.-   3) Example 3-3 of EP 2 327 707 A discloses a reaction of    tetrabutylammonium bromide, trimethylsilyl cyanide and boron    trichloride in p-xylene at 150° C. for 30 hours, with a yield of    98%. The molar ratio of boron compound:TMSCN was 1:5.5.-   4) Example 3-11 of EP 2 327 707 A discloses a reaction of boron    trifluoride diethyl ether, tetrabutylammonium bromide and    trimethylsilylcyanide at 170° C. for 30 hours, with a yield of 75%.    But not all embodiments which fall under claim 7 actually work well:    Example 3 of the instant invention shows one embodiment also    starting with boron trifluoride diethyl ether, which falls under    claim 7, but produces the desired [B(CN)₄] salt only as a by-product    in negligible amounts, the main product is a [BF(CN)₃] salt.

There was a need for a simplified method with high yield andsatisfactory purity for the preparation of fluoro cyanide compounds ofthe 13th group of the periodic table with the anion having the generalformula [(Z¹F_(4−m)(CN)_(m))⁻] with Z¹ is B, Al, Ga, In or Tl and mbeing 1, 2, 3 or 4. The boron source should be a readily availablecompound with low costs. The cyanide source should not be a metalcyanide to avoid its negative impact on the environment. The number ofreactants should be small and the method should allow the conversionwithout the presence of a solvent. The content of Cl and Br in the finalproduct should be low. Also the content of Si and cyanide in the finalproduct should be low. The method should require as few steps aspossible. The method should allow also the preparation of compounds withm being 1, 2, 3 or 4 and not only of either a compound with m being 3 ora compound with m being 4. The method should avoid the use of Cl₂, AgCNor AgBF₄. The method should provide stable compounds of said formulawhich can be used as ionic liquids or as precursors of ionic liquids andcan be used e.g. in electrolyte formulations and in electrochemical oroptoelectronic devices. These compounds should be able to be disposed ofin an environmentally friendly manner after use.

The method should allow the preparation of the desired compounds in highyields and under mild conditions with respect to methods disclosed inthe prior art.

This object is achieved by a method using trimethylsilylcyanide as CNsource and by doing the reaction in the presence of a Lewis acid. NoCl₂, AgCN or AgBF₄ is required. The content of Cl, Br, Si and cyanide inthe final product is low. Another advantage is that the reaction doesnot require an extra solvent. The method has a reduced number of stepscompared to the methods known from the prior art. The method allows forthe preparation not only of compounds with m being only 3 or only 4, butfor compounds with n being 1, 2, 3 or 4. These compounds can be preparedspecifically and individually, and not only as mixtures. The reactioncan be done under milder conditions than those used in the methods ofthe prior art, the reaction can be done at lower temperature or inshorter time.

In this text, the following meanings are used, if not otherwise stated:

-   -   alkyl linear or branched alkyl;    -   C_(1-q) alkyl refers to any alkyl residue which contains from 1        to q carbon atoms; for example C₁₋₆ alkyl encompasses inter alia        methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl,        tert-butyl, n-pentyl, isopentyl (3-methylbutyl), neopentyl        (2,2-dimethylpropyl), n-hexyl and isohexyl (4-methylpentyl);    -   C_(2-q) alkenyl refers to an alkenyl residue which contains from        2 to q carbon atoms and contains at least one double bond, the        carbon chain can be linear or branched; for example C₂₋₄ alkenyl        encompasses inter alia ethenyl, 1-methylethenyl, prop-1-enyl,        prop-2-enyl, 2-methylprop-2-enyl and buta-1,3-dienyl;    -   C_(2-q) alkynyl refers to an alkynyl residue which contains from        2 to q carbon atoms and contains at least one triple bond, the        carbon chain can be linear or branched; for example C₂₋₄ alkynyl        encompasses inter alia ethynyl, prop-1-ynyl and prop-2-ynyl;    -   C₆₋₁₀ aryl refers to an aryl residue which has from 6 to 10        carbon atoms and is unsubstituted or substituted by 1, 2, 3 or 4        identical or different substituents independently from each        other selected from the group consisting of C₁₋₄ alkyl and C₁₋₄        alkoxy; for example C₆₋₁₀ aryl encompasses inter alia phenyl,        methylphenyl, methoxyphenyl, dimethylphenyl, ethylmethylphenyl,        diethylphenyl and naphthyl;    -   cyclic alkyl or cycloalkyl include cyclo and polycyclo, such as        bicyclo or tricyclo, aliphatic residues;    -   C_(3-q) cycloalkyl refers to a cycloalkyl group having from 3 to        q carbon atoms; for example C₃₋₁₀ cycloalkyl encompasses inter        alia cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,        cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl;    -   C_(1-q) alkoxy refers to an linear or branched alkoxy group        having from 1 to q carbon atoms; for example C₁₋₂₀ alkoxy        encompasses inter alia methoxy, ethoxy, propoxy, isopropoxy,        n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy,        1,4-dimethylpentyloxy, hexyloxy, heptyloxy, octyloxy,        1,5-dimethylhexyloxy, nonyloxy, decyloxy,        4-ethyl-1,5-dimethylhexyloxy, undecyloxy, dodecyloxy,        tridecyloxy, tetradecyloxy and eicosyloxy;    -   alkylene means a linear or branched alkylene group; e.g.        propylene, and e.g.

propylene can be connected via its C1 and C2 carbon atoms (a branchedalkylene group), or via its C1 and C3 carbon atoms (linear alkylenegroup);

-   -   BMMIm n-Butyl-2-methyl-3-methylimidazolium

-   -   BMPy n-Butylmethylpyridinium

-   -   BMPyrr n-Butylmethylpyrrolidinium

-   -   BMPip n-Butylmethylpiperidinium

-   -   DCM dichloromethane;    -   EMIm 1-ethyl-3-methylimidazolium

-   -   eq. molar equivalent;    -   halide F⁻, Cl⁻, Br⁻ or I⁻, preferably F⁻, Cl⁻ or Br⁻, more        preferably Cl⁻;    -   halogen F, Cl, Br or I; preferably F, Cl or Br;    -   HEIm 1-ethylimidazolium

-   -   IL ionic liquid;    -   “linear” and “n-” are used synonymously with respect to the        respective isomers of alkanes;    -   RT room temperature, it is used synonymously with the expression        ambient temperature;    -   T_(dec) decomposition temperature;    -   THF tetrahydrofuran;    -   TMSCN (CH₃)₃SiCN, i.e. trimethylsilylcyanide;    -   Trityl means the trityl cation, i.e. [Ph₃C⁺]    -   “wt %”, “% by weight” and “weight-%” are used synonymously and        mean percent by weight.    -   The expressions dye sensitized solar cell and photosensitized        solar cell are used synonymously.

SUMMARY OF THE INVENTION

Subject of the invention is a method for the preparation of compound offormula (I);[Cat^(n+)][(Z¹F_(4-m)(CN)_(m))⁻]_(n)  (I)the method comprises a step (St1);step (St1) comprises a reaction (Real), wherein [(Z¹F₄)⁻] is reactedwith trimethylsilylcyanide in the presence of CATLEWISACID and in thepresence of Cat^(n+);CATLEWISACID is a Lewis Acid selected from the group consisting of LewisAcid from the 1., 2., 3., 4., 5., 6., 7., 8., 9., 10., 11., 12., 13.,14., 15. and 16. group of the periodic table, zeolite, guanidinium andmixtures thereof;

-   -   Z¹ is selected from the group consisting of B, Al, Ga, In and        Tl;    -   m is 1, 2, 3 or 4;    -   n is 1, 2, 3 or 4;    -   Cat^(n+) is selected from the group consisting of inorganic        cation CatINORG^(n+) and organic cation CatORG^(n+);    -   CatINORG^(n+) is a cation selected from the 1., 2., 3., 4., 5.,        6., 7., 8., 9., 10., 11., 12., 13., 14., 15. or 16. group of the        periodic table, or is a cation from the lanthanides or is a        cation from the actinides or is NH₄ ⁺;    -   CatORG^(n+) is selected from the group consisting of CatORG-A⁺,        CatORG-B⁺, CatORG-C⁺, [(CH₃)₃SiFSi(CH₃)₃]⁺, Ph₃C⁺, guanidinium        and (H₂(R18)N-R16-N(R19)H₂)²⁺;    -   CatORG-A⁺ is (WR2R3R4R5)⁺,        wherein    -   W is a nitrogen or phosphorus; and    -   (i) R2, R3, R4 and R5 are identical or different and        independently from each other selected from the group consisting        of H, C₁₋₂₀ alkyl, C₁₋₂₀ perfluoroalkyl, C₃₋₁₀ cycloalkyl and        C₆₋₁₀ aryl, with the proviso, that at least one of the residues        R2, R3, R4 and R5 is not H; or    -   (ii) R2 and R3 together are a hydrocarbon chain and form        together with W a 5- to 7-membered saturated or unsaturated        heterocyclic ring,    -   R4 and R5 are identical or different and independently from each        other selected from the group consisting of H, C₁₋₂₀ alkyl,        C₁₋₂₀ perfluoroalkyl, C₃₋₁₀ cycloalkyl and C₆₋₁₀ aryl; or    -   (iii) R2 and R3 together are a hydrocarbon chain and form        together with W, and R4 and R5 together are a hydrocarbon chain        and form together with W, independently from each other, 5- to        7-membered saturated or unsaturated heterocyclic rings;    -   CatORG-B⁺ is (XR6R7R8)⁺,        wherein    -   X is nitrogen,    -   R6 and R7 together are a hydrocarbon chain and form together        with X a 5- to 7-membered unsaturated heterocyclic ring in which        X is connected by a single bond and a double bond to R6 and R7        respectively,    -   R8 is selected from the group consisting of H, C₁₋₂₀ alkyl, C₂₋₈        alkenyl, C₁₋₂₀ perfluoroalkyl, C₃₋₁₀ cycloalkyl or C₆₋₁₀ aryl;    -   CatORG-C⁺ is (YR9R1OR11)⁺,        wherein    -   Y is sulphur;    -   R9, R10 and R11 are identical or different and independently        from each other selected from the group consisting of H, C₁₋₂₀        alkyl, C₁₋₂₀ perfluoroalkyl, C₃₋₁₀ cycloalkyl and C₆₋₁₀ aryl; or    -   (ii) R9 and R10 together are a hydrocarbon chain and form        together with Y a 5- to 7-membered saturated or unsaturated        ring,    -   R11 is selected from the group consisting of H, C₁₋₂₀ alkyl,        C₁₋₂₀ perfluoroalkyl, C₃₋₁₀ cycloalkyl and C₆₋₁₀ aryl;    -   the residues R2, R3, R4, R5, R6, R7, R8, R9, R10 and R11 are,        independently from each other, unsubstituted or, where        applicable, substituted by 1, 2, 3, 4, 5 or 6 substituents        selected from the group consisting of C₁₋₄ alkyl, C₃₋₁₀        cycloalkyl, C₂₋₈ alkenyl, phenyl, benzyl, halogen, cyano and        C₁₋₄ alkoxy;    -   in any of said hydrocarbon chains formed by R2 and R3, by R4 and        R5, by R6 and R7, by R9 and R10, 1 or 2 carbon atoms of said        hydrocarbon chains can be exchanged for 1 or 2 heteroatoms        respectively, said one or two heteroatoms being selected from        the group consisting of O, N and S; in case of an exchange for        N, this N is unsubstituted or substituted by a residue selected        from the group consisting of C₁₋₈ alkyl, C₃₋₁₀ cycloalkyl, C₂₋₈        alkenyl and C₁₋₈ perfluoroalkyl;    -   R16 is selected from the group consisting of C₂₋₈ alkylen, C₃₋₈        cycloalkylen, phenylen, C(H)(phenyl), R17(—O-R17)_(n1);    -   R17 is selected from the group consisting of CH₂—CH₂,        CH₂—CH₂—CH₂, CH₂—C(H)(CH₃)—CH₂, CH₂—CH₂—C(H)(CH₃) and        CH₂—CH₂—CH₂—CH₂;    -   R18 and R19 are identical or different and independently from        each other selected from the group consisting of H, C₁₋₈ alkyl,        C₃₋₈ cycloalkyl, phenyl and benzyl;    -   n1 is an integer from 1 to 20.

DETAILED DESCRIPTION OF THE INVENTION

-   -   Preferably, Z¹ is B, also in connection with any of the        embodiments disclosed in the specification.    -   Preferably, m is 2, 3 or 4;    -   more preferably, m is 3 or 4;    -   also in connection with any of the embodiments disclosed in the        specification.

Preferably, n is 1 or 2, also in connection with any of the embodimentsdisclosed in the specification.

-   -   Preferably, CATLEWISACID is selected from the group consisting        of [(CH₃)₃SiFSi(CH₃)₃]⁺, Q1(R27)₃, guanidinium, (R26)₃C⁺,        adamantyl cation, [(R24)₃O]⁺, [(R25)₃Si]⁺, Q2(R36)(R28)₃,        Q3(R29)₃, Q4(R30)₅, Q5(R32)₃, Q6(R33)₂, Q7(R31), Q8(R34)₂,        Q9(R35)₃, Q10(R37)₂, Q11(R38), zeolite and mixtures thereof;    -   Q1 is selected from the group consisting of B, Al and Ga;    -   R27 is selected from the group consisting of C₁₋₁₀ alkoxy,        halogen, C₁₋₁₀ alkyl, CN, SCN and C₆F₅;    -   R24 is C₁₋₁₀ alkyl;    -   R25 is C₁₋₁₀ alkyl;    -   R26 is selected from the group consisting of CN, SCN, Ph and        C₁₋₁₀ alkyl;    -   Q2 is selected from the group consisting of Si and Ti;    -   R28 and R36 are identical or different and independently from        each other selected from the group consisting of C₁₋₁₀ alkoxy,        halogen, C₁₋₁₀ alkyl, CN, SCN and C₆F₅;    -   Q3 is selected from the group consisting of P, Sb and Bi;    -   R29 is selected from the group consisting of C₁₋₁₀ alkoxy,        halogen, CN, SCN, C₁₋₁₀ alkyl and C₆F₅;    -   Q4 is selected from the group consisting of P, Sb and Nb;    -   R30 is selected from the group consisting of C₁₋₁₀ alkoxy,        halogen, CN, SCN, C₁₋₁₀ alkyl and C₆F₅;    -   Q5 is selected from the group consisting of Cr and Fe;    -   R32 is selected from the group consisting of halogen, CN and        SCN;    -   Q6 is selected from the group consisting of Mn, Fe, Pd and Pt;    -   R33 is selected from the group consisting of halogen, CN and        SCN;    -   Q7 is Cu or Ag;    -   R31 is selected from the group consisting of halogen, CN and        SCN;    -   Q8 is selected from the group consisting of Cu, Zn, Cd and Hg;    -   R34 is selected from the group consisting of halogen, CN, and        SCN;    -   Q9 Sc or Ln;    -   R35 is selected from the group consisting of halogen, CN, and        SCN;    -   Q10 Ca;    -   R37 is halogen;    -   Q11 K;    -   R38 is halogen;    -   more preferably, CATLEWISACID is selected from the group        consisting of [(CH3)3SiFSi(CH₃)₃]⁺, Si(Cl)(C₆H₅)₃, B(R27)₃,        Al(R27)₃, GaF₃, GaCl₃, guanidinium, (R26)₃C⁺, [(R24)₃O]⁺,        [(R25)₃Si]⁺, Si(R28)₄, TiF₄, TiCl₄, Q3(halogen)₃, Q3(CN)₃,        Q3(C₁₋₄ alkyl)₃, Q4(halogen)₅, Q4(C₁₋₁₀ alkyl)₅, Cr(Cl)₃,        Fe(halogen)₃, Mn(Cl)₂, Fe(halogen)₂, Pd(halogen)₂, Pt(halogen)₂,        Pd(CN)₂, Pt(CN)₂, Pd(SCN)₂, Pt(SCN)₂, AgCl, AgCN, CuCl, CuCl₂,        CuF, CuBr, CuCN, CuF₂, CuBr₂, Cu(CN)₂, ZnF₂, ZnCl₂, ZnBr₂,        Zn(CN)₂, ScF₃, ScCl₃, ScBr₃, LnF₃, LnCl₃, LnBr₃, CaCl₂, KF,        zeolite and mixtures thereof;    -   even more preferably, CATLEWISACID is selected from the group        consisting of [(CH3)3SiFSi(CH₃)₃]⁺, Si(Cl)(C₆H₅)₃, B(R27)₃,        Al(R27)₃, GaF₃, GaCl₃, (R26)₃C⁺, [(R24)₃O]⁺, [(R25)₃Si]⁺,        Si(halogen)₄, Si(C₁₋₁₀ alkyl)₄, TiF₄, TiCl₄, P(halogen)₃,        P(CN)₃, Sb(halogen)₃, Bi(halogen)₃, Bi(CN)₃, P(halogen)₅,        P(C₁₋₁₀ alkyl)₅, Sb(halogen)₅, Nb(halogen)₅, CrCl₃, FeF₃, FeCl₃,        FeBr₃, MnCl₂, FeF₂, FeCl₂, FeBr₂, PdF₂, PdCl₂, PdBr₂, PtF₂,        PtCl₂, PtBr₂, AgCN, CuCl, CuCl₂, CuF, CuBr, CuCN, CuF₂, ZnF₂,        ZnCl₂, ZnBr₂, Zn(CN)₂, ScF₃, ScCl₃, LnF₃, LnCl₃, CaCl₂, KF,        zeolite and mixtures thereof;    -   especially, CATLEWISACID is selected from the group consisting        of [(CH₃)₃SiFSi(CH₃)₃]⁺, Si(Cl)(C₆H₅)₃, BF₃, BCl₃, BBr₃, B(C₁₋₄        alkyl)₃, B(C₆F₅)₃, AlF₃, AlCl₃, Al(C₁₋₄ alkyl)₃, Al(C₆F₅)₃,        GaF₃, GaCl₃, (Ph)₃C⁺, (CH₃)₃C⁺, [(C₁₋₃ alkyl)₃O]⁺, [(C₁₋₄        alkyl)₃Si]⁺, Si(halogen)₄, Si(C₁₋₁₀ alkyl)₄, TiF₄, TiCl₄,        P(halogen)₃, P(CN)₃, SbF₃, SbI₃, BiF₃, BiI₃, Bi(CN)₃,        P(halogen)₅, SbF₅, NbF₅, NbCl₅, CrCl₃, FeCl₃, FeBr₃, MnCl₂,        FeCl₂, FeBr₂, PdCl₂, PdBr₂, PtCl₂, PtBr₂, AgCN, CuCl, CuCl₂,        CuF, CuF₂, ZnF₂, ZnCl₂, ZnBr₂, Zn(CN)₂, ScF₃, ScCl₃, LnF₃,        LnCl₃, CaCl₂, KF, zeolite and mixtures thereof;    -   more especially, CATLEWISACID is selected from the group        consisting of [(CH₃)₃SiFSi(CH₃)₃]³⁰ , Si(Cl)(C₆H₅)₃, BF₃, BCl₃,        B(C₁₋₄ alkyl)₃, B(C₆F₅)₃, AlCl₃, GaF₃, GaCl₃, (Ph)₃C⁺, (CH₃)₃C⁺,        [(C₁₋₄ alkyl)₃Si]⁺, SiF₄, SiCl₄, Si(C₁₋₈ alkyl)₄, TiF₄, TiCl₄,        PCl₃, PBr₃, PI₃, P(CN)₃, SbF₃, SbI₃, Bi(CN)₃, PF₅, PCl₅, PBr₅,        PI₅, SbF₅, NbCl₅, CrCl₃, FeCl₃, FeBr₃, MnCl₂, FeCl₂, FeBr₂,        PdCl₂, PdBr₂, PtCl₂, PtBr₂, AgCN, CuCl, CuCl₂, CuF, CuF₂, ZnF₂,        Zn(CN)₂, ScF₃, ScCl₃, LnF₃, LnCl₃, CaCl₂, KF, zeolite and        mixtures thereof;    -   even more especially, CATLEWISACID is selected from the group        consisting of [(CH3)3SiFSi(CH₃)₃]⁺, Si(Cl)(C₆H₅)₃, BF₃, BCl₃,        B(C₆F₅)₃, AlCl₃, GaF₃, GaCl₃, Ph₃C⁺, [(C₁₋₄ alkyl)₃Si]⁺, SiF₄,        SiCl₄, Si(C₁₋₄ alkyl)₄, TiF₄, TiCl₄, PCl₃, PBr₃, PI₃, P(CN)₃,        SbF₃, SbI₃, Bi(CN)₃, PF₅, PCl₅, PBr₅, PI₅, SbF₅, NbCl₅, CrCl₃,        FeCl₃, FeBr₃, MnCl₂, FeCl₂, FeBr₂, PdCl₂, PdBr₂, PtCl₂, PtBr₂,        AgCN, CuCl, CuCl₂, CuF, CuF₂, ZnF₂, ScF₃, ScCl₃, LnF₃, LnCl₃,        CaCl₂, KF, zeolite and mixtures thereof;    -   in particular, CATLEWISACID is selected from the group        consisting of [(CH3)3SiFSi(CH₃)₃]⁺, Si(Cl)(C₆H₅)₃, BF₃, BCl₃,        B(C₆F₅)₃, AlCl₃, GaF₃, GaCl₃, Ph₃C⁺, [(ethyl)₃Si]⁺, SiCl₄, TiF₄,        TiCl₄, P(CN)₃, SbF₃, Bi(CN)₃, PF₅, PCl₅, SbF₅, NbCl₅, CrCl₃,        FeCl₃, MnCl₂, AgCN, CuCl, CuCl₂, ZnF₂, CaCl₂, KF, zeolite and        mixtures thereof;    -   more in particular, CATLEWISACID is selected from the group        consisting of [(CH3)3SiFSi(CH₃)₃]⁺, Si(Cl)(C₆H₅)₃, BF₃, GaF₃,        GaCl₃, [(ethyl)₃Si]⁺, Ph₃C⁺, SiCl₄, TiF₄, TiCl₄, P(CN)₃, PF₅,        PCl₅, SbF₅, NbCl₅, CrCl₃, FeCl₃, MnCl₂, AgCN, CaCl₂, KF, SiC1₄,        zeolite and mixtures thereof;    -   even more in particular, CATLEWISACID is selected from the group        consisting of [(CH₃)₃SiFSi(CH₃)₃]⁺, Si(Cl)(C₆H₅)₃, BF₃, GaF₃,        GaCl₃, [(ethyl)₃Si]⁺, Ph₃C⁺, SiCl₄, TiF₄, TiCl₄, P(CN)₃, PF₅,        PCl₅, SbF₅, NbCl₅, CrCl₃, FeCl₃, MnCl₂, SiCl₄, zeolite and        mixtures thereof;    -   in a very preferred embodiment, CATLEWISACID is selected from        the group consisting of B(F)₃, GaF₃, GaCl₃, [(ethyl)₃Si]⁺,        Pn₃C⁺, TiF₄, TiCl₄, PF₅, PCl₅, [(C₁₋₄ alkyl)₃Si]⁺,        [(CH₃)₃SiFSi(CH₃)₃]⁺, Sb(F)₅, zeolite and mixtures thereof;    -   in a more very preferred embodiment, CATLEWISACID is        [(CH₃)₃SiFSi(CH₃)₃]⁺, GaF₃, GaCl₃, [(ethyl)₃Si]⁺, Ph₃C⁺, TiF₄,        TiCl₄, PF₅, PCl₅, zeolite or mixtures thereof;    -   in an even more very preferred embodiment, CATLEWISACID is        [(CH₃)₃SiFSi(CH₃)₃]⁺, GaF₃, GaCl₃, Ph₃C⁺, TiF₄, TiCl₄, PF₅,        PCl₅, zeolite or mixtures thereof;    -   in an especially very preferred embodiment, CATLEWISACID is        GaF₃, GaCl₃, Ph₃C⁺, TiF₄, TiCl₄, PF₅, PCl₅, zeolite or mixtures        thereof.        Preferably,    -   Q1 is B.        Preferably,    -   R24 is C₁₋₄ alkyl;    -   R25 is C₁₋₇ alkyl;    -   R26 is selected from the group consisting of Ph and C₁₋₄ alkyl;    -   R27 is selected from the group consisting of C₁₋₇ alkoxy, Cl, F,        Br, C₁₋₇ alkyl and C₆F₅;        more preferably,    -   R24 is C₁₋₃ alkyl;    -   R25 is C₁₋₅ alkyl;    -   R26 is selected from the group consisting of Ph and C₁₋₂ alkyl;    -   R27 is selected from the group consisting of C₁₋₄ alkoxy, Cl, F,        C₁₋₄ alkyl and C₆F₅;        even more preferably,    -   R24 is methyl or ethyl;    -   R25 is C₁₋₄ alkyl;    -   R26 is Ph or methyl;    -   R27 is selected from the group consisting of C₁₋₃ alkoxy, Cl, F,        C₁₋₃ alkyl and C₆F₅.    -   In another preferred embodiment, CATLEWISACID is selected from        the group consisting of [(CH3)3SiFSi(CH₃)₃]⁺, Ph₃C⁺, B(C₆F₅)₃,        and mixtures thereof;        more preferably, CATLEWISACID is Ph₃C .        Preferably, CATLEWISACID is used in the reaction (Real) in form        of a catalyst CAT;    -   CAT is a Lewis Acid selected from the group consisting of Lewis        Acid from the 1., 2., 3., 4., 5., 6., 7., 8., 9., 10., 11., 12.,        13., 14., 15. and 16. group of the periodic table, zeolite,        guanidinium[ANIO] and mixtures thereof;    -   more preferably, CAT is selected from the group consisting of        [(CH₃)₃SiFSi(CH₃)₃][ANIO], Q1(R27)₃, guanidinium[ANIO],        (R26)₃C[ANIO], adamantyl[ANIO], [(R24)₃O][ANIO],        [(R25)₃Si][ANIO], Q2(R36)(R28)₃, Q3(R29)₃, Q4(R30)₅, Q5(R32)₃,        Q6(R33)₂, Q7(R31), Q8(R34)₂, Q9(R35)₃, Q10(R37)₂, Q11(R38),        zeolite and mixtures thereof;    -   even more preferably, CAT is selected from the group consisting        of [(CH₃)₃SiFSi(CH₃)₃][ANIO], Si(Cl)(C₆H₅)₃, B(R27)₃, Al(R27)₃,        GaF₃, GaCl₃, guanidinium[ANIO], (R26)₃C[ANIO], [(R24)₃O][ANIO],        [(R25)₃Si][ANIO], Si(R28)₄, TiF₄, TiCl₄, Q3(halogen)₃, Q3(CN)₃,        Q3(C₁₋₄ alkyl)₃, Q4(halogen)₅, Q4(C₁₋₁₀ alkyl)₅, Cr(Cl)₃,        Fe(halogen)₃, Mn(Cl)₂, Fe(halogen)₂, Pd(halogen)₂, Pt(halogen)₂,        Pd(CN)₂, Pt(CN)₂, Pd(SCN)₂, Pt(SCN)₂, AgCl, AgCN, CuCl, CuCl₂,        CuF, CuBr, CuCN, CuF₂, CuBr₂, Cu(CN)₂, ZnF₂, ZnCl₂, ZnBr₂,        Zn(CN)₂, ScF₃, ScCl₃, ScBr₃, LnF₃, LnCl₃, LnBr₃, CaCl₂, KF,        zeolite and mixtures thereof;    -   especially, CAT is selected from the group consisting of        [(CH₃)₃SiFSi(CH₃)₃][ANIO], Si(Cl)(C₆H₅)₃, B(R27)₃, Al(R27)₃,        GaF₃, GaCl₃, (R26)₃C[ANIO], [(R24)₃O][ANIO], [(R25)₃Si][ANIO],        Si(halogen)₄, Si(C₁₋₁₀ alkyl)₄, TiF₄, TiCl₄, P(halogen)₃,        P(CN)₃, Sb(halogen)₃, Bi(halogen)₃, Bi(CN)₃, P(halogen)₅,        P(C₁₋₁₀ alkyl)₅, Sb(halogen)₅, Nb(halogen)₅, CrCl₃, FeF₃, FeCl₃,        FeBr₃, MnCl₂, FeF₂, FeCl₂, FeBr₂, PdF₂, PdCl₂, PdBr₂, PtF₂,        PtCl₂, PtBr₂, AgCN, CuCl, CuCl₂, CuF, CuBr, CuCN, CuF₂, ZnF₂,        ZnCl₂, ZnBr₂, Zn(CN)₂, ScF₃, ScCl₃, LnF₃, LnCl₃, CaCl₂, KF,        zeolite and mixtures thereof;    -   more especially, CAT is selected from the group consisting of        [(CH₃)₃SiFSi(CH₃)₃][ANIO], Si(Cl)(C₆H₅)₃, BF₃, BCl₃, BBr₃,        B(C₁₋₄ alkyl)₃, B(C₆F₅)₃, AlF₃, AlC1₃, Al(C₁₋₄ alkyl)₃,        Al(C₆F₅)₃, GaF₃, GaCl₃, (Ph)₃C[ANIO], (CH₃)₃C[ANIO], [(C₁₋₃        alkyl)₃O][ANIO], [(C₁₋₄ alkyl)₃Si][ANIO], Si(halogen)₄, Si(C₁₋₁₀        alkyl)₄, TiF₄, TiCl₄, P(halogen)₃, P(CN)₃, SbF₃, SbI₃, BiF₃,        BiI₃, Bi(CN)₃, P(halogen)₅, SbF₅, NbF₅, NbCl₅, CrCl₃, FeCl₃,        FeBr₃, MnCl₂, FeCl₂, FeBr₂, PdCl₂, PdBr₂, PtCl₂, PtBr₂, AgCN,        CuCl, CuCl₂, CuF, CuF₂, ZnF₂, ZnCl₂, ZnBr₂, Zn(CN)₂, ScF₃,        ScCl₃, LnF₃, LnCl₃, CaCl₂, KF, zeolite and mixtures thereof;    -   even more especially, CAT is selected from the group consisting        of [(CH₃)₃SiFSi(CH₃)₃][ANIO], Si(Cl)(C₆H₅)₃, BF₃, BCl₃, B(C₁₋₄        alkyl)₃, B(C₆F₅)₃, AlCl₃, GaF₃, GaCl₃, (Ph)₃C[ANIO],        (CH₃)₃C[ANIO], [(C₁₋₄ alkyl)₃Si][ANIO], SiF₄, SiCl₄, Si(C₁₋₈        alkyl)₄, TiF₄, TiCl₄, PCl₃, PBr₃, PI₃, P(CN)₃, SbF₃, SbI₃,        Bi(CN)₃, PF₅, PCI₅, PBr₅, PI_(S), SbF₅, NbCl₅, CrCl₃, FeCl₃,        FeBr₃, MnCl₂, FeCl₂, FeBr₂, PdCl₂, PdBr₂, PtCl₂, PtBr₂, AgCN,        CuCl, CuCl₂, CuF, CuF₂, ZnF₂, Zn(CN)₂, ScF₃, ScCl₃, LnF₃, LnCl₃,        CaCl₂, KF, zeolite and mixtures thereof;    -   in particular, CAT is selected from the group consisting of        [(CH₃)₃SiFSi(CH₃)₃][ANIO], Si(Cl)(C₆H₅)₃, BF₃, BCl₃, B(C₆F₅)₃,        AlCl₃, GaF₃, GaCl₃, Ph₃C[ANIO], [(C₁₋₄ alkyl)₃Si][ANIO], SiF₄,        SiCl₄, Si(C₁₋₄ alkyl)₄, TiF₄, TiCl₄, PCl₃, PBr₃, PI₃, P(CN)₃,        SbF₃, SbI₃, Bi(CN)₃, PF₅, PCl₅, PBr₅, PI₅, SbF₅, NbCl₅, CrCl₃,        FeCl₃, FeBr₃, MnCl₂, FeCl₂, FeBr₂, PdCl₂, PdBr₂, PtCl₂, PtBr₂,        AgCN, CuCl, CuCl₂, CuF, CuF₂, ZnF₂, ScF₃, ScCl₃, LnF₃, LnCl₃,        CaCl₂, KF, zeolite and mixtures thereof;    -   more in particular, CAT is selected from the group consisting of        [(CH₃)₃SiFSi(CH₃)₃][ANIO], Si(Cl)(C₆H₅)₃, BF₃, BCl₃, B(C₆F₅)₃,        AlCl₃, GaF₃, GaCl₃, Ph₃C[ANIO], SiCl₄, TiF₄, TiCl₄, P(CN)₃,        SbF₃, Bi(CN)₃, PF₅, PCl₅, SbF₅, NbCl₅, CrCl₃, FeCl₃, MnCl₂,        AgCN, CuCl, CuCl₂, ZnF₂, CaCl₂, KF, zeolite and mixtures        thereof;    -   even more in particular, CAT is selected from the group        consisting of [(CH₃)₃SiFSi(CH₃)₃][ANIO], Si(Cl)(C₆H₅)₃, BF₃,        B(C₆F₅)₃ GaF₃, GaCl₃, Ph₃C[ANIO], SiCl₄, TiF₄, TiCl₄, P(CN)₃,        PF₅, PCl₅, SbF₅, NbCl₅, CrCl₃, FeCl₃, MnCl₂, AgCN, CaCl₂, KF,        SiC1₄, zeolite and mixtures thereof;    -   very even more in particular, CAT is selected from the group        consisting of [(CH₃)₃SiFSi(CH₃)₃][ANIO], Si(Cl)(C₆H₅)₃, BF₃,        B(C₆F₅)₃ GaF₃, GaCl₃, Ph₃C[ANIO], SiCl₄, TiF₄, TiCl₄, P(CN)₃,        PF₅, PCl₅, SbF₅, NbCl₅, CrCl₃, FeCl₃, MnCl₂, SiCl₄, zeolite and        mixtures thereof;    -   in a very preferred embodiment, CAT is selected from the group        consisting of BF₃, B(C₆F₅)₃ GaF₃, GaCl₃, TiF₄, TiCl₄, PF₅, PCl₅,        [(CH₃)₃SiFSi(CH₃)₃][ANIO], Ph₃C[ANIO], Sb(F)₅, zeolite and        mixtures thereof;    -   in a more very preferred embodiment, CAT is        [(CH₃)₃SiFSi(CH₃)₃][ANIO], B(C₆F₅)₃ GaF₃, GaCl₃, TiF₄, TiCl₄,        PF₅, PCl₅, Ph₃C[ANIO], zeolite or mixtures thereof;    -   in an even more very preferred embodiment, CAT is        [(CH₃)₃SiFSi(CH₃)₃][ANIO], B(C₆F₅)₃ GaF₃, GaCl₃, TiF₄, TiCl₄,        PF₅, PCl₅, Ph₃C[ANIO], zeolite or mixtures thereof;    -   in an especially very preferred embodiment, CAT is B(C₆F₅)₃        GaF₃, GaCl₃, TiF₄, TiCl₄, PF₅, PCl₅, Ph₃C[ANIO], zeolite or        mixtures thereof;    -   ANIO is selected from the group consisting of        [P(R40)_(6-m1)(R41)_(m1)]⁻, [B(R42)_(4-m2)(R43)_(m2)]⁻, F⁻, Cl⁻,        Br⁻, I⁻, CN⁻ and SCN⁻;    -   R40 and R41 are identical of different in independently from        each other selected from the group consisting of CN, SCN, F, Cl,        Br and I;    -   m1 is 0, 1, 2, 3, 4 or 5;    -   R42 and R43 are identical of different in independently from        each other selected from the group consisting of C₆F₅, CN, SCN,        F, Cl, Br and I;    -   m2 is 0, 1, 2 or 3;    -   preferably, ANIO is selected from the group consisting of        P(R40)₆ ⁻, B(R42)₄ ⁻, F⁻, Cl⁻, Br⁻, I⁻, CN⁻ and SCN⁻;    -   R40 is selected from the group consisting of CN, SCN, F, Cl, Br        and I;    -   R42is selected from the group consisting of C₆F₅, CN, SCN, F,        Cl, Br and I;    -   more preferably, ANIO is selected from the group consisting of        P(R40)₆ ⁻, B(R42)₄ ⁻, F⁻, Cl⁻, Br⁻, CN⁻ and SCN⁻;    -   R40 is selected from the group consisting of CN, SCN, F, Cl and        Br;    -   R42is selected from the group consisting of C₆F₅, CN, SCN, F, Cl        and Br;    -   with Q1, R27, R24, R25, R26, Q2, R28, R36, Q3, R29, Q4, R30, Q5,        R32, Q6, R33, Q7, R31, Q8, R34, Q9, R35, Q10, R37, Q11 and R38        as defined herein, also with all their embodiments.

Preferably, [ANIO] is [B(C₆F₅)₄] or [BF₄].

-   -   Special embodiments of CAT are [(CH₃)₃SiFSi(CH₃)₃][B(C₆F₅)₄],        Si(Cl)(C₆H₅)₃, BF₃, B(C₆F₅)₃, GaF₃, GaCl₃, Ph₃C[BF₄], SiCl₄,        TiF₄, TiCl₄, P(CN)₃, PF₅, PCl₅, SbF₅, NbCl₅, CrCl₃, FeCl₃,        MnCl₂, AgCN, CaCl₂, KF, SiCl₄, zeolite and mixtures thereof;    -   very even more in particular, CAT is selected from the group        consisting of [(CH₃)₃SiFSi(CH₃)₃][B(C₆F₅)₄], Si(Cl)(C₆H₅)₃, BF₃,        B(C₆F₅)₃, GaF₃, GaCl₃, Ph₃C[BF₄], SiCl₄, TiF₄, TiCl₄, P(CN)₃,        PF₅, PCl₅, SbF₅, NbCl₅, CrCl₃, FeCl₃, MnCl₂, SiCl₄, zeolite and        mixtures thereof;    -   in a very preferred embodiment, CAT is selected from the group        consisting of [(CH₃)₃SiFSi(CH₃)₃][B(C₆F₅)₄], BF₃, B(C₆F₅)₃ GaF₃,        GaCl₃, TiF₄, TiCl₄, PF₅, PCl₅, Sb(F)₅, zeolite and mixtures        thereof;    -   in a more very preferred embodiment, CAT is        [(CH₃)₃SiFSi(CH₃)₃][B(C₆F₅)₄], B(C₆F₅)₃ GaF₃, GaCl₃, TiF₄,        TiCl₄, PF₅, PCl₅, Ph₃C[BF₄], zeolite or mixtures thereof;    -   in a even more very preferred embodiment, CAT is B(C₆F₅)₃, GaF₃,        GaCl₃, TiF₄, TiCl₄, PF₅, PCl₅, Ph₃C[BF₄], zeolite or mixtures        thereof.    -   In another preferred embodiment, CAT is selected from the group        consisting of (CH₃)₃SiFSi(CH₃)₃[B(C₆F₅)₄], [Ph₃C][BF₄], B(C₆F₅)₃        and mixtures thereof;    -   more preferably, CAT is [Ph₃C][BF₄].    -   CATLEWISACID and CAT respectively can be used in immobilized        form on a carrier CARR;    -   CARR is a carrier conventionally used for immobilizing catalysts        in heterogeneously catalyzed reactions;    -   preferably, CARR is selected from the group consisting of        epoxide, polystyrene, zeolite, activated carbon and metal oxide;    -   said metal oxide is preferably selected from the group        consisting of MnO₂, Fe₂O₃, CO₃O₄, NiO, CuO, CuMnO₂, MgO, Al₂O₃,        SiO₂, V₂O₅, MoO₃, WO₃ and mixed oxides thereof.    -   Zeolite can be any zeolite, preferably montmorrilonte or        bentonite, more preferably Montmorillonite K10®, BASF, Germany        (also available at Sigma Aldrich, CAS Number 1318-93-0).

Preferably, Cat^(n+) is, more preferably Cat^(n+) and [(Z¹F₄)⁻] are,used in the reaction (Real) in form of a compound of formula (A1);[Cat^(n+)][(Z¹F₄)⁻]_(n)  (A1)whereinCat^(n+), Z¹ and n are defined herein, also with all their embodiments.

-   -   In a preferred embodiment, compound of formula (A1) is reacted        with trimethylsilylcyanide in the presence of a catalyst CAT;    -   with compound of formula (A1) and catalyst CAT as defined        herein, also with all their embodiments;    -   preferably, catalyst CAT is (CH₃)₃SiFSi(CH₃)₃[B(C₆F₅)₄] or        [Ph₃C][BF₄],    -   more preferably, catalyst CAT is [Ph₃C][BF₄];    -   in one preferred embodiment, compound of formula (A1) is        different from catalyst CAT;    -   in another preferred embodiment, compound of formula (A1) is        identical with catalyst CAT.

Compound of formula (A1) and catalyst CAT can be one and the samecompound, that means compound of formula (A1) can act simultaneously ascatalyst CAT and vice versa.

-   -   Preferably, CatINORG^(n+) is a cation selected from the 1., 2.,        3., 4., 5., 6., 7., 8., 9., 10., 11., 12., 13., 14. or 15. group        of the periodic table or is a cation from the lanthanides or is        NH₄ ⁺;    -   more preferably, CatINORG^(n+) is a cation selected from the 1.,        2., 4., 5., 6., 7., 8., 9., 10., 11., 12., 13., 14. or 15. group        of the periodic table or is a cation from the lanthanides or NH₄        ⁺;    -   even more preferably, CatINORG^(n+) is selected from the group        consisting of Li⁺, Na⁺, K⁺, Rb⁺, Cs⁺, Be²⁺, Mg²⁺, Ca²⁺, Sr²⁺,        Ba²⁺, Ti⁴⁺, Ti³⁺, Zr⁴⁺, Zr³⁺, Hf⁴⁺, Hf³⁺, V⁴⁺, V³⁺, V²⁺, Nb⁴⁺,        Ta⁴⁺, Cr³⁺, Mo⁴⁺, Mo³⁺, Mo²⁺, W⁴⁺, W³⁺, W²⁺, Mn⁴⁺, Mn³⁺, Mn²⁺,        Fe⁴⁺, Fe³⁺, Fe²⁺, Ru⁴⁺, Ru³⁺, Ru²⁺, OS⁴⁺, OS³⁺, OS²⁺, Co⁴⁺,        Co³⁺, Co²⁺, Rh⁴⁺, Rh³⁺, Ir⁴⁺, Ir³⁺, Ni⁴⁺, Ni³⁺, Ni²⁺, Pd⁴⁺,        Pd³⁺, Pd²⁺, Pt⁴⁺, Pt³⁺, Pt²⁺, Cu⁴⁺, Cu³⁺, Cu²⁺, Cu⁺, Ag⁴⁺, Ag³⁺,        Ag²⁺, Ag⁺, Au³⁺, Au²⁺, Au⁺, Zn²⁺, Zn⁺, Cd²⁺, Cd⁺, Hg²⁺, Hg⁺,        B³⁺, Al³⁺, Ga³⁺, Ga⁺, In³⁺, In³⁺, Ti³⁺, Ti⁺, Ge⁴⁺, Ge²⁺, Sn⁴⁺,        Sn²⁺, Pb⁴⁺, Pb²⁺, As³⁺, Sb³⁺, Bi³⁺, Bi¹⁺, La³⁺, Nb³⁺, Sm³⁺,        Eu³⁺, Gd³⁺, and NH₄ ⁺;    -   especially, CatINORG^(n+) is selected from the group consisting        of Li⁺, Na⁺, K⁺, Mg²⁺, Ca²⁺, Ti⁴⁺, Ti³⁺, Zr⁴⁺, Zr³⁺, V⁴⁺, V³⁺,        V²⁺, Cr³⁺, Mo⁴⁺, Mo³⁺, Mo²⁺, W⁴⁺, W³⁺, W²⁺, Mn⁴⁺, Mn³⁺, Mn²⁺,        Fe⁴⁺, Fe³⁺, Fe²⁺, Ru⁴⁺, Ru³⁺, Ru²⁺, Co⁴⁺, Co³⁺, Co²⁺, Rh⁴⁺,        Rh³⁺, Ir⁴⁺, Ir³⁺, Ni⁴⁺, Ni³⁺, Ni²⁺, Pd⁴⁺, Pd³⁺, Pd²⁺, Pt⁴⁺,        Pt³⁺, Pt²⁺, Cu⁴⁺, Cu³⁺, Cu²⁺, Cu⁺, Ag⁴⁺, Ag³⁺, Ag²⁺, Ag⁺, Zn²⁺,        Zn⁺, Al³⁺, Ga³⁺, Ga⁺, In³⁺, In⁺, Sn⁴⁺, Sn²⁺, Pb⁴⁺, Pb²⁺, Sb³⁺,        Nb³⁺, Sm³⁺, Eu³⁺, Gd³⁺, and NH₄ ⁺;    -   more especially, CatINORG^(n+) is selected from the group        consisting of Li⁺, Na⁺, K⁺, Mg²⁺, Ca²⁺, Ti⁴⁺, V⁴⁺, V³⁺, V²⁺,        Cr³⁺, Fe⁴⁺, Fe³⁺, Fe²⁺, Co⁴⁺, Co³⁺, Co²⁺, Cu⁴⁺, Cu³⁺, Cu²⁺, Cu⁺,        Ag²⁺, Ag⁺, Zn²⁺, Zn⁺, Al³⁺, Sn⁴⁺, Sn²⁺, Pb⁴⁺, Pb²⁺, Sb³⁺, Eu³⁺,        Gd³⁺, and NH₄ ⁺;    -   even more especially, CatINORG^(n+) is selected from the group        consisting of Li⁺, Na⁺, K⁺, Mg²⁺, Ca²⁺, Ti⁴⁺, V⁴⁺, V³⁺, Cr³⁺,        Fe⁴⁺, Fe³⁺, Fe²⁺, Co⁴⁺, Co³⁺, Co²⁺, Cu⁴⁺, Cu³⁺, Cu²⁺, Cu⁺, Ag⁺,        Zn²⁺, Al³⁺, Sn⁴⁺, Sn²⁺, Pb⁴⁺, Pb²⁺, Gd³⁺, and NH₄ ⁺;    -   in particular, CatINORG^(n+) is selected from the group        consisting of Li⁺, Na⁺, K⁺, NH₄ ⁺, Ag⁺, Mg²⁺, Ca²⁺, Zn²⁺and        Cu²⁺;    -   more in particular, CatINORG^(n+) is selected from the group        consisting of Li⁺, Na⁺, K⁺, NH₄ ⁺, Ag⁺, Mg²⁺, Ca²⁺ and Zn²⁺;    -   even more in particular, CatINORG^(n+) is Li⁺, Na⁺, K⁺, Ag⁺,        Mg²⁺, or Zn²⁺;    -   especially in particular, CatINORG^(n+) is Li⁺, K⁺, Ag⁺, Mg²⁺,        or Zn²⁺;    -   more especially in particular, CatINORG^(n+) is Li⁺, K⁺ or Ag⁺.

Preferably, n in CatInORG^(n+) is 1 or 2.

-   -   The term “where applicable” in the definition of CatORG^(n+)        means, that any of the optional substituents of the residues R2        to R11 requires a respective site, and e.g. in case of R2 being        a perfluorinated side chain no respective site is available any        more for a substituent.    -   Preferably, CatORG^(n+) contains a heteroatom selected from the        group consisting of nitrogen, phosphorus, sulfur and oxygen;    -   more preferably, CatORG^(n+) contains a heteroatom selected from        the group consisting of nitrogen and phosphorus.        Preferably,    -   R16 is selected from the group consisting of C₂₋₆ alkylen, C₅₋₆        cycloalkylen, phenylen, C(H)(phenyl), R17(—O-R17)_(n1);    -   R17 is selected from the group consisting of CH₂—CH₂,        CH₂—CH₂—CH₂ and CH₂—CH₂—CH₂—CH₂;    -   R18 and R19 are identical or different and independently from        each other selected from the group consisting of H, C₁₋₄ alkyl,        C₅₋₆ cycloalkyl, phenyl and benzyl;    -   n1 is an integer from 1 to 10;        more preferably,    -   R16 is selected from the group consisting of C₂₋₄ alkylen, C₆        cycloalkylen, phenylen, C(H)(phenyl), R17(—O-R17)_(n1);    -   R17 is selected from the group consisting of CH₂—CH₂ and        CH₂—CH₂—CH₂;    -   R18 and R19 are identical and selected from the group consisting        of H, C₁₋₄ alkyl, C₅₋₆ cycloalkyl, phenyl and benzyl;    -   n1 is an integer from 1 to 6;        even more preferably, for n being 2 CatORG^(n+) is        (H₂(R18)N-R16-N(R19)H₂)²⁺;    -   R16 is selected from the group consisting of C₂₋₄ alkylen,        phenylen and C(H)(phenyl);    -   R18 and R19 are identical and selected from the group consisting        of H, C₁₋₄ alkyl, C₅₋₆ cycloalkyl, phenyl and benzyl;        especially, when n is 2, then CatORG^(n+) is        (H₃N—CH₂—CH₂—NH₃)²⁺.    -   Preferably, n in CatORG^(n+) is 1.    -   Preferably, CatORG^(n+) is selected from the group consisting of        ammonium, phosphonium, sulfonium, pyrrolidinium, pyrrolinium,        pyrrolium, pyrazolium, pyrazolinium, imidazolium, imidazolinium,        triazolium, oxazolium, thiazolium, piperidinium, piperazinium,        morpholinium, pyridinium, pyridazinium, pyrimidinium,        pyrazinium, 1,3-dioxolium, pyrylium, thiopyrylium,        quinoxalinium, indolinium, indolium, [(CH₃)₃SiFSi(CH₃)₃]⁺,        Ph₃C⁺, and mixtures thereof;    -   more preferably from the group consisting of ammonium,        phosphonium, sulfonium, pyrrolidinium, pyrrolinium, pyrrolium,        pyrazolium, imidazolium, triazolium, oxazolium, thiazolium,        piperidinium, piperazinium, morpholinium, pyridinium,        pyridazinium, pyrimidinium, pyrazinium, 1,3-dioxolium, pyrylium,        thiopyrylium, [(CH₃)₃SiFSi(CH₃)₃]⁺, Ph₃C⁺, and mixtures thereof.    -   More preferably, CatORG^(n+) is selected from the group        consisting of

[N(R20)(R21)(R22)R23]⁺, [P(R20)(R21)(R22)R23]⁺, [(CH₃)₃SiFSi(CH₃)₃]⁺,Ph₃C⁺, and mixtures thereof;wherein

-   -   R20, R21, R23 are identical or different and independently from        each other selected from the group consisting of H, C₁₋₂₀ alkyl,        C₃₋₁₀ cycloalkyl and allyl;    -   R22 is C₁₋₂₀ alkyl, C₃₋₁₀ cycloalkyl or allyl;        preferably,    -   R20, R21, R23 are identical or different and independently from        each other selected from the group consisting of H, C₁₋₁₄ alkyl,        C₅₋ ₈ cycloalkyl and allyl;    -   R22 is C₁₋₁₄ alkyl, C₅₋₈ cycloalkyl or allyl;        more preferably,    -   R20, R21, R23 are identical or different and independently from        each other selected from the group consisting of H, C₁₋₈ alkyl,        C₅₋₇ cycloalkyl and allyl;    -   R22 is C₁₋₈ alkyl, C₅₋₇ cycloalkyl or allyl;        even more preferably, CatORG^(n+) is selected from the group        consisting of

[NH(C₂H₅)₃]⁺, [NH(C₃H₇)₃]⁺, [NH(C₄H₉)₃]⁺, [N(C₂H₅)₄]⁺, [N(C₃H₇)₄]⁺,[N(C₄H₉)₄]⁺, [P(C₂H₅)₄]⁺, [P(C₃H₇)₄]⁺, [P(C₄H₉)₄]⁺,[P(C₆H₁₃)₃(C₁₄H₂₉)]⁺, [(CH₃)₃SiFSi(CH₃)₃]⁺, Ph₃C⁺, and mixtures thereof;especially, CatORG^(n+) is selected from the group consisting of

[NH(C₂H₅)₃]⁺, [NH(C₄H₉)₃]⁺, [N(C₂H₅)₄]⁺, [NH(C3H7)4]⁺, [N(C₄H₉)₄]⁺,[P(C₂H₅)₄]⁺, [P(C₃H₇)₄]⁺, [P(C₄H₉)₄]⁺, [(CH₃)₃SiFSi(CH₃)₃]⁺, Ph₃C⁺, andmixtures thereof.more especially, CatORG^(n+) is selected from the group consisting of

[NH(C₂H₅)₃]⁺, [NH(C₄H₉)₃]⁺, [N(C₂H₅)₄]⁺, [N(C₃H₇)₄]⁺, [N(C₄H₉)₄]⁺,[P(C₂H₅)₄]⁺, [P(C₃H₇)₄]⁺, [P(C₄H₉)₄]⁺, [(CH₃)₃SiFSi(CH₃)₃]⁺, Ph₃C⁺, andmixtures thereof.

-   -   In particular, Cat^(n+) is a cation (Cat-Part1);    -   cation (Cat-Part1) is CatINORG^(n+) or CatORG^(n+),    -   with CatINORG selected from the group consisting of Li⁺, Na⁺,        K⁺, NH₄ ⁺, Ag⁺, Mg²⁺, Ca²⁺ and Zn²⁺;        and        with CatORG^(n+) selected from the group consisting of

[NH(C₂H₅)₃]⁺, [NH(C₄H₉)₃]⁺, [N(C₂H₅)₄]⁺, [N(C₃H₇)₄]⁺, [N(C₄H₉)₄]⁺,[P(C₂H₅)₄]⁺, [P(C₃H₇)₄]⁺, [P(C₄H₉)₄]⁺, [(CH₃)₃SiFSi(CH₃)₃]⁺, Ph₃C⁺, andmixtures thereof.Even more preferably, compound of formula (I) is compound (Group-I),

-   -   compound (Group-I) is selected from the group consisting of        compound of formula (Ia) and compound of formula (Ib);        [Cat^(n+)][(BF(CN)₃)⁻]_(n)  (Ia)        [Cat^(n+)][(B(CN)₄)^(')]_(n)  (Ib)    -   Cat^(n+) and n are as defined above, also with all their        embodiments, preferably Cat^(n+) is cation (Cat-Part1).    -   A special embodiment of compound of formula (I) is compound        (GROUP-II), compound (GROUP-II) is selected from the group        consisting of K⁺[(BF(CN)₃)⁻], Ag⁺[(BF(CN)₃)⁻], Li⁺[(BF(CN)₃)⁻],        Mg²⁺[(BF(CN3)⁻]₂, Ca²⁺[(BF(CN)₃)⁻]₂, [N(n-Pr)₄]⁺[(BF(CN)₃)⁻],        [N(n-Bu)₄]⁺[(BF(CN)₃)⁻], [P(n-Bu)₄]⁺[(BF(CN)₃)⁻],        1,3-dimethylimidazolium [(BF(CN)₃)⁻],        1-ethyl-3-methylimidazolium [(BF(CN)₃)⁻],        1-propyl-3-methylimidazolium [(BF(CN)₃)⁻] and mixtures thereof.    -   Another special embodiment of compound of formula (I) is        compound (GROUP-III), compound (GROUP-III) is selected from the        group consisting of K⁺[((B(CN)₄)⁻], Ag⁺[((B(CN)₄)⁻],        Li⁺[((B(CN)₄)⁻], Mg²⁺[(B(CN)₄)⁻]₂, Ca²⁺[(B(CN)₄)⁻]₂,        [N(n-Pr)₄]⁺[(B(CN)₄)⁻], [N(n-Bu)₄]⁺[(B(CN)₄)⁻],        [P(n-Bu)₄]⁺[(B(CN)₄)⁻], 1,3-dimethylimidazolium [(B(CN)₄)⁻],        1-ethyl-3-methylimidazolium [(B(CN)₄)⁻],        1-propyl-3-methylimidazolium [(B(CN)₄)⁻] and mixtures thereof.    -   Yet another special embodiment of compound of formula (I) is        compound (GROUP-IV), compound (GROUP-IV) is selected from the        group consisting of K⁺[((B(F)₂(CN)₂)⁻], Ag⁺[((B(F)₂(CN)₂)⁻],        Li⁺[(B(F)₂(CN)₂)⁻], Mg²⁺[(B(F)₂(CN)₂)⁻]₂, Ca²⁺[(B(F)₂(CN)₂)⁻]₂,        [N(n-Pr)₄]⁺[(B(F)₂(CN)₂)⁻], [N(n-Bu)₄]⁺[(B(F)₂(CN)₂)⁻],        [P(n-Bu)₄]⁺[(B(F)₂(CN)₂)⁻], 1,3-dimethylimidazolium        [(B(F)₂(CN)₂)⁻], 1-ethyl-3-methylimidazolium [(B(F)₂(CN)₂)⁺],        1-propyl-3-methylimidazolium [(B(F)₂(CN)₂)⁻] and mixtures        thereof.    -   Another special embodiment of compound of formula (I) is        compound (GROUP-V), compound (GROUP-V) is selected from the        group consisting of K⁺[((B(F)₃(CN))⁻], Ag⁺[((B(F)₃(CN))⁻],        Li⁺[((B(F)₃(CN))⁻], Mg²⁺[(B(F)₃(CN))⁻]₂, Ca²⁺[(B(F)₃(CN))⁻]₂,        [N(n-Pr)₄]⁺[(B(F)₃(CN))⁻], [N(n-Bu)₄]⁺[(B(F)₃(CN))⁻],        [P(n-Bu)₄]⁺[(B(F)₃(CN))⁻], 1,3-dimethylimidazolium        [(B(F)₃(CN))⁻], 1-ethyl-3-methylimidazolium [(B(F)₃(CN))⁻],        1-propyl-3-methylimidazolium [(B(F)₃(CN))⁻] and mixtures        thereof.

In particular, compound of formula (I) is compound (GROUP), compound(GROUP) is selected from the group consisting of compound of formula(1), compound of formula (2), compound of formula (3), compound offormula (4), compound of formula (5), compound of formula (6), compoundof formula (7), compound of formula (8), compound of formula (9),compound of formula (10), and mixtures thereof.[(n-Bu)₄N][BF(CN)₃]  (1)[EMIm][BF(CN)₃]  (2)[(n-Bu)₄N][BF₃(CN)]  (3)[(n-Bu)₄N][BF₂(CN)₂]  (4)[(n-Bu)₄N][B(CN)₄]  (5)K[BF(CN)₃]  (6)K[B(CN)₄]  (7)[BMIm][B(CN)₄]  (8)Li[BF(CN)₃]  (9)Li[B(CN)₄]  (10)

Preferably, from 1 to 40 mol equivalents, more preferably 4 to 35 molequivalents, even more preferably from 6 to 25 mol equivalents,especially from 6 to 15 mol equivalents, of trimethylsilylcyanide areused in reaction (Rea1), the mol equivalents being based on the molaramount of the anion [(Z¹F₄)⁻].

Preferably, when CATLEWISACID is an uncharged compound, then the molaramount of Cat^(n+) is equal to the molar amount of anion [(Z¹F₄)⁻].

Preferably, when CATLEWISACID is a cation, then the combined molaramount of CATLEWISACID and Cat^(n+) is 1-fold to 40-fold, morepreferably 1-fold to 35-fold, even more preferably 1-fold to 25-foled,especially 1-fold to 15-fold, more especially 1-fold to 10-fold, evenmore especially 1-fold to 5-fold, in particular 1-fold to 2-fold, of themolar amount of the anion [(Z¹F₄)⁻].

Preferably, from 0.0001 to 40 mol equivalents, more preferably 0.001 to35 mol equivalents, even more preferably from 0.005 to 25 molequivalents, especially from 0.005 to 25 mol equivalents, moreespecially from 0.005 to 15 mol equivalents, even more especially from0.005 to 5 mol equivalents, of CATLEWISACID are used in reaction (Rea1),the mol equivalents being based on the molar amount of the anion[(Z¹F₄)⁻].

In another preferable embodiment, from 0.01 to 40 mol %, more preferably0.1 to 35 mol %, even more preferably 0.1 to 25 mol %, especially from0.5 to 15 mol %, more especially from 0.5 to 10 mol %, even moreespecially from 0.5 to 5 mol %, of CATLEWISACID are used in reaction(Rea1), the mol % being based on the molar amount of the anion[(Z¹F₄)⁻].

When reaction (Rea1) is done by reacting compound of formula (A1) withtrimethylsilylcyanide in the presence of a catalyst CAT, and

when compound of formula (A1) is different from catalyst CAT, then

-   -   preferably, from 1 to 40 mol equivalents, more preferably 4 to        35 mol equivalents, even more preferably from 5 to 25 mol        equivalents, especially from 5 to 15 mol equivalents, more        especially from 5 to 10 mol equivalents, of        trimethylsilylcyanide are used in reaction (Rea1), the mol        equivalents being based on the molar amount of compound of        formula (A1); and    -   preferably, from 0.01 to 40 mol %, more preferably 0.1 to 35 mol        %, even more preferably 0.1 to 25 mol %, especially from 0.5 to        15 mol %, more especially from 0.5 to 10 mol %, even more        especially from 0.5 to 5 mol %, of catalyst CAT are used in        reaction (Rea1), the mol % being based on the combined molar        amount of compound of formula (A1) and catalyst CAT;        whereas when compound of formula (A1) is identical with catalyst        CAT, then    -   preferably, from 1 to 40 mol equivalents, more preferably 4 to        35 mol equivalents, even more preferably from 5 to 25 mol        equivalents, especially from 5 to 15 mol equivalents, more        especially from 5 to 10 mol equivalents, of        trimethylsilylcyanide are used in reaction (Rea1), the mol        equivalents being based on the combined molar amount of compound        of formula (A1) and catalyst CAT.

The reaction temperatures of reaction (Rea1) is preferably from −75 to150° C., more preferably from −50 to 120° C., more preferably from −50to 100° C., even more preferably −50 to 80° C.

Another possible range of the reaction temperatures of reaction (Rea1)is preferably from −10 to 150° C., more preferably from −10 to 120° C.,more preferably from 0 to 100° C., even more preferably 10 to 80° C.

Reaction (Rea1) can be done in a closed system and at the pressurecaused by the chosen temperature.

The reaction time of reaction (Rea1) is preferably from 15 min to 96 h,more preferably from 20 min to 85 h, even more preferably from 20 min to48 h.

Another possible range of the reaction time of reaction (Rea1) ispreferably from 30 min to 96 h, more preferably from 1 h to 85 h, evenmore preferably from 1 h to 48 h.

Preferably, reaction (Rea1) is done under inert atmosphere. Preferably,the inert atmosphere is achieved by the use if an inert gas preferablyselected from the group consisting of argon, another noble gas, lowerboiling alkane, nitrogen and mixtures thereof.

The lower boiling alkane is preferably a C₁₋₃ alkane, i.e. methane,ethane or propane.

After the reaction, compound of formula (I) can be isolated by standardmethods such as evaporation of volatile components, extraction, washing,drying, concentration, crystallization, chromatography and anycombination thereof, which are known per se to the person skilled in theart.

Preferably, after the reaction the reaction product is treated withhydrogen peroxide, preferably with aqueous hydrogen peroxide.

More preferably for isolation, the reaction product is mixed withaqueous hydrogen peroxide to provide a mixture (M).

Preferably, the concentration of the aqueous hydrogen peroxide is from10 to 40 wt % hydrogen peroxide, the wt % based on the total weight ofthe aqueous hydrogen peroxide.

Preferably, from 1 to 30 mol equivalents, more preferably from 1 to 20mol equivalents, of hydrogen peroxide are used, the mol equivalentsbeing based on the molar amount of compound of formula (A1).

Preferably mixture (M) is stirred for 5 min to 12 h, more preferably for10 min to 6 h.

Preferably mixture (M) is stirred at a temperature (M), temperature (M)is preferably from ambient temperature to 100° C.

After treatment with hydrogen peroxide, mixture (M) is preferablyfiltrated. The residue of the filtration is preferably washed with asolvent (WASH), solvent (WASH) is preferably water or an ether such asdiethylether, more preferably diethylether.

-   -   Preferably, the method comprises additionally to step (St1) a        step (St2), step (St2) is done after step (St1);        step (St2) comprises a reaction (Rea2), reaction (Rea2) is a        metathesis reaction wherein cation Cat^(n+) in compound of        formula (I) is exchanged for a cation different from Cat^(n+);        compound of formula (I) having been prepared in step (St1);        Cat^(n+), n, compound of formula (I) and step (St1) are as        defined above, also with all their embodiments.

Preferably, reaction (Rea2) provides for the preparation of a compoundof formula (I-Cat-r);[Cat-r^(r+)][(Z¹F_(4-m)(CN)_(m))⁻]_(r)  (I-Cat-r)

-   -   Cat-r^(r+) is selected from the group consisting of        CatINORG^(n+) and CatORG^(n+) and is different from Cat^(n+);    -   r is 1, 2, 3 or 4;        with step (St1), Z¹, m, CatINORG^(n+) and CatORG^(n+) as defined        above, also with all their embodiments.

Preferably, in reaction (Rea2) Cat^(n+) is exchanged for Cat-r^(r+) froma compound of formula (I-Cat-n);(Cat-r^(r+))_(t1)(AnINORG^(q−))_(t2)  (I-Cat-n)

-   -   q is 1 or 2;    -   t1 is 1 or 2;    -   t2 is 1, 2, 3 or 4;    -   when r is 1 and q is 1, then t1 is 1 and t2 is 1;    -   when r is 2 and q is 1, then t1 is 1 and t2 is 2;    -   when r is 3 and q is 1, then t1 is 1 and t2 is 3;    -   when r is 4 and q is 1, then t1 is 1 and t2 is 4;    -   when r is 1 and q is 2, then t1 is 2 and t2 is 1;    -   when r is 2 and q is 2, then t1 is 1 and t2 is 1;    -   when r is 3 and q is 2, then t1 is 2 and t2 is 3;    -   when r is 4 and q is 2, then t1 is 1 and t2 is 2;    -   AnINORG^(q−) is an anion selected from the group consisting of        halide, OH⁻, CN⁻, OCN⁻, SCN⁻, N₃ ⁻, sulfate, hydrogensulfate,        nitrate, CO₃ ²⁻, HCO₃ ⁻, BF₄ ⁻, PF₆ ⁻, SbF₆ ⁻, CF₃SO₃ ⁻,        (CF₃SO₂)₂N⁻, (FSO₂)₂N⁻, C₁₋₆ alkyl-SO₃ ⁻, C₁₋₆ alkyl-O-SO₃ ⁻,

anions of C₁₋₂₀ monocarboxylic aliphatic acids, mono- and dianions ofC₂₋₆ dicarboxylic aliphatic acids, anions of benzoic acids, mono- anddianions of phthalic acids, of isophthalic acids and of terephthalicacids, N(CN)₂ ⁻, C(CN)₃ ⁻, B(CN)₄ ⁻, P(CN)₆ ⁻, Sb(CN)₆ ⁻, and mixturesthereof;

-   -   Cat-r^(r+), r, CatINORG^(n+) and CatORG^(n+) are as defined        above, also with all their embodiments.    -   Reaction (Rea2) is a metathesis reaction, also called a        salt-exchange reaction. In a metathesis reaction such as        reaction (Rea2) a first cation in a first salt is exchanged for        a second cation, said second cation coming from a second salt.    -   Preferably, AnINORG^(q−) is an anion selected from the group        consisting of halide, OH⁻, CN⁻, sulfate, hydrogensulfate,        nitrate, CO₃ ²⁻, HCO₃ ⁻, BF₄ ⁻, PF₆ ⁻, CF₃SO₃ ⁻, (CF₃SO₂)₂N⁻,        (FSO₂)₂N⁻, H₃C—SO₃ ⁻, H₃C—CH₂—SO₃ ⁻, H₃C—O—SO₃ ⁻, H₃C—CH₂—O—SO₃        ⁻, acetate, oleate, fumarate, maleate, oxalate, benzoate, N(CN)₂        ⁻, and mixtures thereof;    -   more preferably, AnINORG^(q−) is an anion selected from the        group consisting of Br⁻, Cl⁻, OH⁻, CN⁻, sulfate,        hydrogensulfate, CO₃ ²⁻, HCO₃ ⁻, acetate, and mixtures thereof;    -   even more preferably, AnINORG^(q−) is an anion selected from the        group consisting of Cl⁻, OH⁻, CN⁻, sulfate, hydrogensulfate, CO₃        ²⁻, HCO₃ ⁻, acetate, and mixtures thereof.    -   In another preferred embodiment, AnINORG^(q−) is an anion        selected from the group consisting of halide, OH⁻, CN⁻, OCN⁻,        SCN⁻, N₃ ⁻, sulfate, hydrogensulfate, nitrate, CO₃ ²⁻, HCO₃ ⁻,        BF₄ ⁻, PF₆ ⁻, SbF₆ ⁻, CF₃SO₃ ⁻, (CF₃SO₂)₂N⁻, (FSO₂)₂N⁻, C₁₋₆        alkyl-SO₃ ⁻, C₁₋₆ alkyl-O-SO₃ ⁻,

anions of C₁₋₂₀ monocarboxylic aliphatic acids, anions of C₂₋₆dicarboxylic aliphatic acids, benzoate, phthalates, N(CN)₂ ⁻, C(CN)₃ ⁻,B(CN)₄ ⁻, P(CN)₆ ⁻, Sb(CN)₆ ⁻, and mixtures thereof.Preferably, r is 1 or 2.

In case of reaction (Rea2), preferably a compound of formula (I-Cat-r)with Cat-r^(r+) being CatORG^(n+) is prepared by exchange of a Cat^(n+)being a CatINORG^(n+) in compound of formula (I) for a CatORG^(n+).

Said CatORG^(n+) is provided in reaction (Rea2) preferably in form of acompound of formula (I-CatORG)(CatORG^(n+))_(q)(AnINORG^(q−))_(n)  (I-CatORG)whereinCat^(n+), n, CatORG^(n+), CatINORG^(n+), q and AnINORG^(q−) are asdefined above, also with all their embodiments.

-   -   Preferably, in reaction (Rea2) the cation different from        Cat^(n+), that is preferably Cat-r^(r+), is present in at least        such a molar amount relative to the molar amount of Cat^(n+) as        required for a stoichiometric exchange of said two cations;    -   more preferably, compound of formula (I) and compound of formula        (I-Cat-n) are present in at least such a molar amount relative        to each other, that Cat^(n+) is stoichiometrically exchanged for        Cat-r^(r+) .    -   Even more preferably, the molar amount of compound of formula        (I-Cat-n) is such, that from 1 to 1.5, even more preferably from        1 to 1.2, required equivalents of Cat-r^(r+) relative to the        equivalents of Cat^(n+) are present.

The reaction temperatures of reaction (Rea2) is preferably from 0 to250° C., more preferably from 10 to 200° C., even more preferably from10 to 150° C., especially from 10 to 100° C., more especially from 10 to50° C.

The reaction (Rea2) is preferably carried out in a solvent (Sol2),solvent (Sol2) is preferably selected from the group consisting ofwater, DCM, ethyl acetate, C₅₋₁₀ alkane, and mixtures thereof.

C₅₋₁₀ alkane is preferably pentane, hexane or heptane.

In a more preferred embodiment, reaction (Rea2) is done in DCM or in abiphasic solvent system of water and DCM.

As an alternative, the reaction can also be carried out in the absenceof a solvent or in a solvent in which the inorganic salt formed as sideproduct is sparingly soluble or insoluble. As a further alternative, itis also possible to carry out the reaction in an aqueous solution usingan ion exchanger loaded with the desired cation Cat^(n+).

The amount of solvent is preferably from 2 to 40 fold, more preferablyfrom 3 to 20 fold, of the weight of compound of formula (I).

Reaction (Rea2) can be done in a closed system and at the pressurecaused by the chosen temperature.

The reaction time of reaction (Rea2) is preferably from 15 min to 96 h,more preferably from 15 min to 48 h, even more preferably from 15 min to24 h.

Preferably, reaction (Rea2) is done under inert atmosphere. Preferably,the inert atmosphere is achieved by the use if an inert gas preferablyselected from the group consisting of argon, another noble gas, lowerboiling alkane, nitrogen and mixtures thereof.

The lower boiling alkane is preferably a C₁₋₃ alkane, i.e. methane,ethane or propane.

Subsequent to reaction (Rea2) there can be a further metathesis reactionor further metathesis reactions.

After reaction (Rea2), compound of formula (I) can be isolated from thereaction mixture by standard methods such as filtration, evaporation ofvolatile components, extraction, washing, drying, concentration,crystallization, chromatography and any combination thereof, which areknown per se to the person skilled in the art.

For example, when reaction (Rea2) was done in a biphasic solvent systemof water and DCM, the aqueous and organic phases are separated, theorganic phase is preferably washed, preferably with water, thenpreferably dried, preferably with Na₂SO₄, K₂CO₃, CaCl₂ or MgSO₄, andfinally evaporated.

Or as another example, when reaction (Rea2) was done in DCM and asuspension was formed, filtration and evaporation of the solvent willisolate the product.

It is possible use compound of formula (I), which was obtained by themethod of instant invention, as substrate in a similar reaction withtrimethylsilylcyanide.

-   -   Therefore the method of instant invention can comprise        additionally to step (St1) a step (St1-1), step (St1-1) is done        after step (St1);    -   step (St1-1) comprises a reaction (Rea1-1), wherein compound of        formula (I), obtained in step (1), is reacted with        trimethylsilylcyanide;    -   preferably the reaction (Rea(1-1) is done in the presence of        CATLEWISACID;    -   with CATLEWISACID as defined above, also in all its embodiments.

Compounds of formula (A1) are commercially available depending on thecation Cat^(n+), e.g. [(n-Bu₄)N][BF₄] and K[BF₄] are commerciallyavailable, as well as catalyst CAT. Other compounds of formula (A1) withcations Cat^(n+) different from K⁺ and (n-Bu₄)N⁺, and which are notcommercially available, can be prepared by conventional metathesisreaction, i.e. substitution of the respective cation K⁺ or (n-Bu₄)N⁺against another cation.

EXAMPLES Methods

¹H, ¹³C, ¹⁹F and ³¹P NMR spectra were recorded on a Bruker AVANCE 300and Bruker AVANCE 250 instruments in CD₃CN, CDCl₃, D₆-DMSO, D₂O orCD₂Cl₂. Chemical shifts are expressed in parts per million referred toTMS in case of ¹H and ¹³C, C¹⁹FCl₃ in case of ¹⁹F, and H₃ ³¹PO₄ in caseof ³¹P, and coupling constants (J) in Hertz. When a % value for theamount of compounds is stated based on NMR measurement, the % valuerepresents an area-%, the area-% being based on the total area of peaksin the spectrum. In case of the individual amount of a component in amixtures the stated % value for the amount of the component in themixture represents an area-%, this area-% being based on the combinedarea of peaks of all components of the mixture; if not stated otherwise.

IR-spectra were recorded on a Nicolet 380 FT-IR spectrometer.Measurements were done at room temperature.

RAMAN-spectra were recorded on a LabRAM HR 800 Horiba Jobin YVON.Measurements were done at room temperature.

The C/H/N-analyses were measured on a C/H/N/S-Analysator (ThermoquestFlash EA 1112).

Melting points and temperature of decomposition T_(dec) were measured ona DSC 823e from Mettler-Toledo. The calibration was carried out with themelting points of In (156.6±0.3° C.) and Zn (419.6±0.7° C.) with anheating rate of 5 K per min.

Preparation Description A: Synthesis of [(n-Bu)₄N][BF₄]

A solution of [(n-Bu₄)N]Br (8.05 g, 24.98 mmol) in 50 ml of CH₂Cl₂ wasadded to the solution of K[BF₄] (3.12 g, 24.78 mmol) in 30 ml of H₂O.After stirring for 24 h at ambient temperature the phases wereseparated. The organic phase was washed three times with 10 ml of water,dried over anhydrous Mg₂SO₄ and filtered. The filtrate was concentratedon a rotary evaporator to obtain a white solid. The obtained solid wasdried at 90° C. in vacuo for 15 hours. The yield of [(n-Bu₄)N][BF₄] was7.83 g (96%, 23.8 mmol).

-   -   DSC (10 Kmin⁻¹): m.p.=153° C.    -   C/H/N Analysis calc. % (found): C 58.36 (58.48), H 11.02        (10.84), N 4.25 (4.13)    -   ¹H NMR (25° C., CD₃CN, 300.13 MHz, delta in ppm): 0.96 (t, 12H,        CH₃), 1.35 (m, 8H, CH₃—CH₂, 1.61 (m, 8H, CH₂—CH₂N), 3.11 (m, 8H,        NCH₂)    -   ¹³C NMR (25° C., CD₃CN, 250.13 MHz, delta in ppm): 14.42 (s, 4C,        CH₃), 20.94 (m, 4C, CH₃—CH₂), 24.95 (m, 4C, CH₂—CH₂N), 59.93 (m,        4C, NCH₂)    -   ¹¹B NMR (25° C., CD₃CN, 96.29 MHz, delta in ppm): −1.18 (s, 1B,        BF₄)    -   ¹⁹F NMR (25° C., CD₃CN, 300.13 MHz, delta in ppm): −151.61 (s,        4F, BF₄)    -   IR (ATR, 32 scans, v in cm⁻¹): 2960 (m), 2935 (w), 2875 (w),        1486 (m), 1468 (w), 1382 (w), 1285 (w), 1152 (w), 1093 (m), 1047        (s), 1034 (s), 881 (w), 800 (w), 739 (w)    -   RAMAN (460 mW, 150 scans, v in cm⁻¹): 2964 (7), 2933 (10), 2876        (10), 2746 (1), 1453 (4), 1327(2), 1153(1), 1137 (2), 911 (2),        880 (1), 766 (1), 256 (2), 79 (1)

Preparation Description B: Synthesis of EMIm[BF₄]

K[BF₄] (0.43 g, 3.4 mmol) and 1-ethyl-3-methylimidazolium bromide (0.50g, 3.4 mmol) were suspended in 50 ml of acetone. After stirring for 24hours under argon atmosphere at ambient temperature the suspension wasfiltered. The solvent was removed in vacuo to obtain a light yellow oil.The product was dried at 90° C. in vacuo for 5 hours to yield 0.61 g(91%, 3.1 mmol) of EMIm[BF₄].

-   -   DSC (10 Kmin⁻¹): m.p.=16° C.    -   C/H/N Analysis calc. % (found): C 36.40 (36.32), H 5.60 (5.58),        N 14.15 (12.90)    -   ¹H NMR (25° C., CD₃CN, 300.13 MHz, delta in ppm): 1.42 (t, 3H,        CH₃), 3.82 (s, 3H, NCH₃), 4.16 (q, 2H, CH₂), 7.37 (m, 1H,        EtNCH), 7.43 (m, 1H, MeNCH), 8.57 (s, 1H, NCHN)    -   ¹³C NMR (25° C., CD₃CN, 300.13 MHz, delta in ppm): 15.53 (s, 1C,        NCH₂—CH₃), 36.73 (s, 1C, NCH₃), 45.80 (s, 1C, NCH₂), 123.01 (s,        1C, EtNCH), 124.64 (s, 1C, MeNCH), 136.98 (s, 1C, NCHN)    -   ¹¹B NMR (25° C., CD₃CN, 96.29 MHz, delta in ppm): −1.11 (s, 1B,        BF₄)    -   ¹⁹F NMR (25° C., CD₃CN, 300.13 MHz, delta in ppm): −151.23 (s,        4F, BF₄)    -   IR (ATR, 32 scans, v in cm⁻¹): 3163 (w), 3122 (w), 2989 (w),        2949 (w), 1574 (m), 1455 (w), 1432 (w), 1392 (w), 1336 (w), 1286        (w), 1170 (m), 1015 (s), 845 (m), 805 (w), 753 (m), 701 (w), 648        (m), 622 (m), 598 (w)

Example 1

[Ph₃C][BF₄] (207 mg, 0.63 mmol) and (CH₃)₃SiCN (625 mg, 6.3 mmol) werestirred at ambient temperatures under argon atmosphere. After two hoursof stirring an ¹¹B NMR was measured. In accordance to ¹¹B NMR theproduct contained only [BF(CN)₃]⁻. After 20 hours of stirring another¹¹B NMR was measured. In accordance to ¹¹B NMR the product containedonly [B(CN)₄]⁻.

Example 2

[EMIm][BF₄] (771 mg, 3.89 mmol), prepared according to PreparationDescription B, [Ph₃C][BF₄] (0.01 g, 0.8 mol %, the mol % being based onthe combined molar amount of [EMIm][BF₄] and [Ph₃C][BF₄]) and (CH₃)₃SiCN(3.87 g, 39 mmol) were stirred under argon atmosphere at ambienttemperatures for Tx h. Then a ¹¹B NMR of the reaction mixture wasmeasured and [Ph₃C][BF₄] was added, in order to have a desired mol% of[Ph₃C][BF₄]. Table 2 shows the details, Tx and the percentage of[BF₃(CN)]⁻[BF₂(CN)₂]⁻ and [BF(CN)₃]⁻ in the reaction mixture accordingto the NMR spectra.

TABLE 2 [Ph₃C][BF₄] [Ph₃C][BF₄] Tx Desired Added [BF₃(CN)]⁻ [BF₂(CN)₂]⁻[BF(CN)₃]⁻ [h] [mol %] [mg] [%] [%] [%] 0 0.8 0.01 — — — 70 1.5 0.02 919 — 87 3 0.04 — 93 7 103 — — — — 100

-   -   Final ¹¹B NMR of EMIm[BF(CN)₃] (25° C., CD₃CN, 96.29 MHz, delta        in ppm): −3.70 (q, 1B, BF₃(CN)), −7.61 (t, 1B, BF₂(CN)₂), −17.88        (d, 1B, BF(CN)₃)

Example 3

[(n-Bu)₄N][BF₄] (1.189 g, 3.6 mmol), prepared according to PreparationDescription A, [Ph₃C][BF₄] (3.6 mol %, the mol % being based on thecombined molar amount of [(n-Bu)₄N][BF₄] and [Ph₃C][BF₄], 44 mg) and(CH₃)₃SiCN (3.55 g, 36 mmol) were stirred under argon atmosphere atambient temperatures for 19 h. The excess (CH₃)₃SiCN and any (CH₃)₃SiFwere removed in vacuo resulting in a light brown crystalline residue,which was suspended in aqueous H₂O₂ (4 ml, 40 mmol, 30 w %), thesuspension was stirred at 70° C. for 1 h. After cooling to ambienttemperature the suspension was filtered. The remaining solid was washedtwo times with water and extracted with 15 ml of CH₂Cl₂. The organiclayer was dried over MgSO₄ and filtered.

After removing the solvent in vacuo a white solid substance was obtainedwhich was washed three times with 5 ml of diethyl ether. The product wasdried at 50° C. in vacuum to yield 1.063 g (84%, 3.03 mmol) of compoundof formula (1).

-   -   C/H/N-Analysis calc. % (found): C 65.14 (65.49), H 10.36        (10.51), N 15.99 (16.29)    -   ¹H NMR (25° C., CD₃CN, 300.13 MHz, delta in ppm): 0.97 (t, 12H,        CH₃), 1.35 (m, 8H, CH₃—CH₂), 1.61 (m, 8H, CH₂—CH₂N), 3.09 (m,        8H, NCH₂)    -   ¹³C NMR (25° C., CD₃CN, 300.13 MHz, delta in ppm): 13.87 (s, 4C,        CH₃), 20.36 (t, 4C, CH₂—CH₃), 24.35 (s, 4C, N—CH₂—CH₂), 59.40        (t, 4C, NCH₂), 127.92 (dq, 3C, BF(CN)₃, ¹J(¹³C-¹¹B)=75 Hz,        ²J(¹³C-¹⁹F)=37 Hz)    -   ¹¹B NMR (25° C., CD₃CN, 96.29 MHz, delta in ppm): −17.86 (d, 1B,        BF(CN)₃)    -   ¹⁹F NMR (25° C., CD₃CN, 300.13 MHz, delta in ppm): −211.68 (q,        F, BF(CN)₃)

Example 4

EMIm[BF₄] (0.739 g, 3.73 mmol), prepared according to PreparationDescription B, [Ph₃C][BF₄] (3.4 mol %, the mol % being based on thecombined molar amount of [EMIm][BF₄] and [Ph₃C][BF₄], 43 mg) and(CH₃)₃SiCN (3.67 g, 37 mmol) were stirred under argon atmosphere atambient temperatures for 20 h. The excess (CH₃)₃SiCN and any (CH₃)₃SiFwere removed in vacuo resulting in a light brown oily residue, which wassuspended in aqueous H₂O₂ (4 ml, 40 mmol, 30 w %), the suspension wasstirred at 70° C. for 1 h. After cooling to ambient temperature 20 mlbutyl acetate was added to the H₂O₂ solution. The resulting mixing wastransferred into centrifuge tubes. After centrifugation (2000 rpm, 2minutes) the supernatant layer was separated. The butyl acetate wasremoved on a rotary evaporator.

The obtained light yellow oil was washed three times with 5 ml ofdiethyl ether. After drying at 70° C. in vacuo 0.694 g (85%, 3.17 mmol)of compound of formula (2) were obtained.

-   -   ¹H NMR (25° C., CD₃CN, 300.13 MHz, delta in ppm): 1.46 (t, 3H,        CH₃), 3.82 (s, 3H, NCH₃), 4.16 (q, 2H, CH₂), 7.32 (m, 1H,        EtNCH), 7.38 (m, 1H, MeNCH), 8.40 (s, 1H, NCHN)    -   ¹¹B NMR (25° C., CD₃CN, 96.29 MHz, delta in ppm): −17.88 (d, 1B,        BF(CN)₃)    -   ¹⁹F NMR (25° C., CD₃CN, 300.13 MHz, delta in ppm): −211.64 (q,        4F, BF(CN)₃)

Example 5

[(n-Bu)₄N][BF(CN)₃] (0.734 g, 2.10 mmol), prepared according to example3, and [Ph₃C][BF₄] (86 mg, 11 mol %, the mol % being based on thecombined molar amount of [(n-Bu)₄N][BF₄] and [Ph₃C][BF₄]) were dissolvedin TMSCN (3.12 g, 31.4 mmol). After Tx hours of stirring at ambienttemperature a ¹¹B NMR and spectrum of the reaction mixture was measuredand [Ph₃C][BF₄] was added, in order to have a desired mol % of[Ph₃C][BF₄]. Table 1 shows the details, Tx and the percentage of[BF(CN)₃]⁻ and [B(CN)₄]⁻ in the reaction mixture according to the NMRspectra.

TABLE 1 [Ph₃C][BF₄] [Ph₃C][BF₄] Tx Desired Added [BF(CN)₃]⁻ [B(CN)₄]⁻[h] [mol %] [mg] [%] [%] 0 11 86 — — 20 17 56 89 11 40 33 198 80 20 88 —— 0 100

-   -   ¹¹B NMR (25° C., CD₃CN, 96.29 MHz, delta in ppm): −17.88 (d, 1B,        BF(CN)₃), −38.59 (s, 1B, B (CN)₄)

Example 8

[(n-Bu)₄N][BF₄] (0.491 g, 1.49 mmol), prepared according to PreparationDescription A, FeCl₃ (20 mg, 7 mol %, the mol % being based on thecombined molar amount of [(n-Bu)₄N][BF₄] and FeCl₃) and (CH₃)₃SiCN (1.58g, 1.59 mmol) were stirred under argon atmosphere at ambient temperaturefor 3 h.

After the stirring at ambient temperature for 3 h an ¹¹B and ¹⁹F NMRspectra were measured. In accordance to ¹⁹F NMR and ¹¹B NMR the productcontained 100% of compound of formula (4).

After removing the solvent the obtained light yellow solid substance wasdried at 50° C. in vacuo to yield 0.400 g (69%, 1.17 mmol) of compoundof formula (4).

-   -   C/H/N Analysis calc. % (found): C 62.97 (62.58), H 10.57        (10.65), N 12.24 (12.35)    -   ¹H NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): 0.99 (t, 12H,        CH₃), 1.41 (m, 8H, CH₃—CH₂), 1.61 (m, 8H, CH₂—CH₂N), 3.13 (m,        8H, NCH₂)    -   ¹¹B NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): −7.2 (q, 1B,        BF₂(CN)₂, ¹J(¹¹B-¹⁹F)=42 Hz)    -   ¹³C NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): 13.3 (s, 4C,        CH₃), 19.4 (t, 4C, CH₂—CH₃), 23.6 (s, 4C, N—CH₂—CH₂), 58.6 (t,        4C, NCH₂)    -   ¹⁹F NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): −153.1 (q,        2F, BF₂(CN)₂, ¹J(¹¹B-¹⁹F)=42 Hz)    -   IR (ATR, 32 scans, v in cm⁻¹): 2966 (m), 2939 (m), 2878 (m),        2210 (m), 1474 (m), 1383 (m), 1242 (w), 1170 (w), 1006 (m), 1050        (s), 1007 (s), 939 (m), 880 (s), 797 (m), 737 (m), 632 (w), 550        (w)

Example 9

Example 8 was repeated with the differences:

-   -   1. MnCl₂ (9 mg, 5 mol %, the mol % being based on the combined        molar amount of [(n-Bu)₄N][BF₄] and MnCl₂) were used instead of        FeCl₃.    -   2. The reaction mixture was stirred for 20 h at ambient        temperature instead of 3 h.        After the stirring for 20 h an ¹¹B and ¹⁹F NMR spectra were        measured. In accordance to ¹⁹F NMR and ¹¹B NMR the product        contained 100% of compound of formula (4).        NMR data was the same as in example 8.

Example 10

Example 8 was repeated with the difference:

-   -   1. PCl₅ (30 mg, 6 mol %, the mol % being based on the combined        molar amount of [(n-Bu)₄N][BF₄] and PCl₅) were used instead of        FeCl₃.        After the stirring for 3 h an ¹¹B and ¹⁹F NMR spectra were        measured. In accordance to ¹⁹F NMR and ¹¹B NMR the product        contained 100% of compound of formula (1).        After removing the solvent the obtained white solid substance        was dried at 50° C. in vacuo to yield 0.680 g (90%, 1.66 mmol)        of compound of formula (1).    -   C/H/N Analysis calc. % (found): C 65.14 (64.44), H 10.36        (10.41), N 15.99 (16.20)    -   ¹H NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): 1.00 (t, 12H,        CH₃), 1.41 (m, 8H, CH₃—CH₂), 1.60 (m, 8H, CH₂—CH₂N), 3.12 (m,        8H, NCH₂)    -   ¹¹B NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): −17.6 (d, 1B,        BF(CN)₃, ¹J(¹¹B-¹⁹F)=45 Hz)    -   ¹³C NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): 13.3 (s, 4C,        CH₃), 19.4 (t, 4C, CH₂—CH₃), 23.6 (s, 4C, N—CH₂—CH₂), 58.7 (t,        4C, NCH₂), 127.2 (dq, 3C, BF(CN)₃, ₁J(¹³C-¹⁹F)=38 Hz,        ¹J(¹³C-¹¹B)=75 Hz)    -   ¹⁹F NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): −210.9 (q,        1F, BF(CN)₃, ¹J(¹¹B-¹⁹F)=45 Hz)    -   IR (ATR, 32 scans, v in cm⁻¹): 2964 (m), 2935 (m), 2876 (m),        2214 (w), 1474 (m), 1381 (m), 1171 (w), 1040 (m), 960 (w), 938        (,), 903 (s), 803 (w), 736 (m), 536 (w)

Example 11

Example 8 was repeated with the difference:

-   -   1. GaCl₃ (30 mg, 5 mol %, the mol % being based on the combined        molar amount of [(n-Bu)₄N][BF₄] and GaCl₃) were used instead of        FeCl₃.    -   2. The reaction mixture was stirred longer then 3 h.        After stirring for 3 h an ¹¹B and ¹⁹F NMR spectra were measured.        In accordance to ¹⁹F NMR and ¹¹B NMR the product contained 99.9%        of compound of formula (1).        NMR data was the same as in example 10.        After further stirring for additional 41 h another ¹¹B NMR        spectra was measured. In accordance to ¹¹B NMR the reaction        mixture contained 93.1% of compound of formula (1) and 6.9% of        compound of formula (5).        NMR data was the same as in example 5.

Example 12

Example 8 was repeated with the difference:

-   -   1. TiCl₄ (0.01 ml, 5 mol %, the mol % being based on the        combined molar amount of [(n-Bu)₄N][BF₄] and TiCl₄) were used        instead of FeCl₃.        After the stirring for 3 h an ¹¹B and ¹⁹F NMR spectra were        measured. In accordance to ¹⁹F NMR and ¹¹B NMR the product        contained 100% of compound of formula (1).        NMR data was the same as in example 10.

Example 13

Example 8 was repeated with the differences:

-   -   1. CrCl₃ (14 mg, 5 mol %, the mol % being based on the combined        molar amount of [(n-Bu)₄N][BF₄] and CrCl₃) were used instead of        FeCl₃.    -   2. The reaction mixture was stirred for 25 h at ambient        temperature instead of 3 h.        After the stirring for 25 h an ¹¹B and ¹⁹F NMR spectra were        measured. In accordance to ¹⁹F NMR and ¹¹B NMR the product        contained 100% of compound of formula (4).        NMR data was the same as in example 8.

Example 15

Example 8 was repeated with the difference:

-   -   1. NbCl₅ (20 mg, 5 mol %, the mol % being based on the combined        molar amount of [(n-Bu)₄N][BF₄] and NbCl₅) were used instead of        FeCl₃.        After the stirring for 3 h an ¹¹B and ¹⁹F NMR spectra were        measured. In accordance to ¹¹B and ¹⁹F NMR the reaction mixture        contained 100% of compound of formula (4).        After further stirring at ambient temperature in addition for        142 h again an ¹¹B and ¹⁹F NMR were measured. In accordance to        ¹¹B and ¹⁹F NMR the reaction mixture contained 56% of compound        of formula (4) and 44% of compound of formula (1).        NMR data was the same as in example 8 and 3.

Example 16

Example 8 was repeated with the difference:

-   -   1. SiCl₄ (0.01 ml, 5 mol %, the mol % being based on the        combined molar amount of [(n-Bu)₄N][BF₄] and SiCl₄) were used        instead of FeCl₃.        After the stirring for 3 h an ¹¹B and ¹⁹F NMR spectra were        measured. In accordance to ¹¹B and ¹⁹F NMR the reaction mixture        contained 100% of compound of formula (4).        NMR data was the same as in example 8.

Example 17

Example 8 was repeated with the difference:

-   -   1. GaCl₃ (30 mg, 5 mol %, the mol % being based on the combined        molar amount of [(n-Bu)₄N][BF₄] and GaCl₃) were used instead of        FeCl₃.    -   2. The reaction mixture was refluxed instead of stirring at        ambient temperature.        After the stirring for 3 h an ¹¹B and ¹⁹F NMR spectra were        measured. In accordance to ¹¹B the reaction mixture contained        100% of compound of formula (5).        After removing the solvent the obtained light yellow solid        substance was dried at 50° C. in vacuo to yield 0.425 g (79%,        1.19 mmol) of compound of formula (5).    -   C/H/N Analysis calc. % (found): C 67.22 (66.43), H 10.15 (9.96),        N 19.60 (19.00)    -   ¹H NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): 1.03 (t, 12H,        CH₃), 1.44 (m, 8H, CH₃—CH₂), 1.62 (m, 8H, CH₂—CH₂N), 3.12 (m,        8H, NCH₂)    -   ¹¹B NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): −38.2 (s, 1B,        B(CN)₄, ¹J(¹¹B-¹⁹F)=71 Hz)    -   ¹³C NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): 13.5 (s, 4C,        CH₃), 19.5 (t, 4C, CH₂—CH₃), 23.6 (s, 4C, N—CH₂—CH₂), 58.7 (t,        4C, NCH₂), 122.5 (q/sept, 4C, B(CN)₄, ¹J(¹¹B-¹³C)=71 Hz,        ¹J(¹⁰B-¹³C)=23 Hz)    -   IR (ATR, 32 scans, v in cm⁻¹): 2964 (m), 2935 (m), 2877 (m),        2214 (w), 1474 (m), 1381 (m), 1168 (w), 1110 (w), 1061 (w), 1035        (w), 991 (m), 967 (m), 931 (s), 886 (m), 802 (w), 735 (m), 535        (w)

Example 18

K[BF₄] (0.67 g, 5.32 mmol), GaCl₃ 6 mol %, the mol % being based on thecombined molar amount of [(n-Bu)₄N][BF₄] and GaCl₃, 63 mg) and(CH₃)₃SiCN (5.8 g, 58.9 mmol) were stirred at ambient temperature for 15h. Then a ¹¹B NMR spectrum of the reaction mixture was measured. Inaccordance to ¹¹B NMR the reaction mixture contained 93% of compound offormula (6) and 7% of K[BF₄].

Then the reaction mixture was refluxed for 9 h and a ¹¹B NMR spectrumwas measured. In accordance to ¹¹B NMR the reaction mixture contained95% of compound of formula (6) and 5% of compound of formula (7).

Example 20

Example 8 was repeated with the differences:

-   -   1. P(CN)₃ (17 mg, 5 mol %, the mol % being based on the combined        molar amount of [(n-Bu)₄N][BF₄] and P(CN)₃) were used instead of        FeCl₃.    -   2. The reaction mixture was stirred for 100 h at ambient        temperature instead of 3 h.        After stirring at ambient temperature for 100 h an ¹¹B and ¹⁹F        NMR spectra were measured. In accordance to ¹⁹F and ¹¹B NMR the        product contained about 95.5% of compound of formula (4) and        4.5% of compound of formula (1).        NMR data was the same as in example 8.

Example 21

Example 17 was repeated with the differences:

-   -   1. 1-Butyl-3-methylimidazolium tetrafluoroborate (1.05 g, 4.65        mmol) were used instead of [(n-Bu)₄][BF₄].    -   2. The reaction mixture was stirred for 2 h at reflux        temperature instead of 3 h.        After the stirring for 2 h an ¹¹B and ¹⁹F NMR spectra were        measured. In accordance to ¹⁹F and ¹¹B NMR the product contained        100% of compound of formula (8).        The excess (CH₃)₃SiCN and any (CH₃)₃SiF were removed in vacuo        resulting in a dark brown oily residue, which was suspended in        aqueous H₂O₂ (7 ml, 70 mmol, 30 w %), the solution was stirred        at 90° C. for 1 h. After cooling to ambient temperature 50 ml        butyl acetate was added to the H₂O₂ solution. The resulting        mixing was transferred into centrifuge tubes. After        centrifugation (2000 rpm, 2 minutes) the supernatant layer was        separated. The butyl acetate was removed on a rotary evaporator.        After drying at 100° C. in vacuo 1.00 g (85%, 3.95 mmol) of        compound of formula (8) were obtained.    -   ¹H NMR (25° C., CD₃CN, 250.13 MHz, delta in ppm): 0.97 (t, 3H,        CH₂—CH₃), 1.37 (m, 2H, CH₂—CH₃), 1.87 (m, 2H, CH₂—CH₂), 3.94 (s,        3H, NCH₃), 4.17 (t, 2H, NCH₂), 7.33 (s, 1H, BuNCH), 7.34 (s, 1H,        MeNCH), 8.44 (s, 1H, NCHN)    -   ¹¹B NMR (25° C., CDCl₃, 80.25 MHz, delta in ppm): −38.4 (s, 1B,        B(CN)₄, ¹J(¹¹B-¹⁹F)=71 Hz)    -   ¹³C NMR (25° C., CD₃CN, 250.13 MHz, delta in ppm): 13.07 (s, 1C,        CH₃), 19.15 (s, 1C, CH₂—CH₃), 31.56 (s, 1C, CH₂—CH₂), 36.39 (s,        1C, NCH₃), 49.94 (s, 1C, NCH₂), 122.3 (q+sep, 4C, B(CN)₄,        ¹J(¹¹B-¹³C)=71 Hz, ¹J(¹⁰B-¹³C)=24 Hz), 122.5 (s, 1C, BuNCH),        123.7 (s, 1C, MeNCH), 135.0 (s, 1C, NCHN)

Table 3

Tabel 3 gives an overview of some of the examples and their results,where the reaction has been done at ambient temperature.

-   -   Ex example    -   m m as in formula (I)    -   t1 reaction time of reaction (Real)    -   [%] is the crude yield according to ¹⁹F NMR, except for those        examples marked with (*), in the reaction mixture before any        isolation or purification    -   (*) in case of the examples marked with (*) the crude yield is        according to ¹¹B NMR instead of ¹⁹F NMR

TABLE 3 m t1 0 1 2 3 4 Ex CAT [h] [%] [%] [%] [%] [%] 11 (*) GaCl₃ 44 —— — 93.1 6.9 12 TiCl₄ 3 — — — 100 — 10 PCl₅ 3 — — — 100 — 20 P(CN)₃ 100— — 95.5 4.5 — 16 SiCl₄ 3 — — 100 — —  8 FeCl₃ 3 — — 100 — — 15 NbCl₅ 3— — 100 — —  9 MnCl₂ 20 — — 100 — — 13 CrCl₃ 25 — — 100 — —

Table 4

Tabel 4 gives an overview of some of the examples and their results,where the reaction has been done at reflux temperature, which was ca.125° C.

-   -   Ex example    -   m m as in formula (I)    -   t1 reaction time of reaction (Real)    -   [%] is the crude yield according to ¹⁹F NMR, except for those        examples marked with (*), in the reaction mixture before any        isolation or purification    -   (*) in case of the examples marked with (*) the crude yield is        according to ¹¹B NMR instead of ¹⁹F NMR

TABLE 4 m t1 0 1 2 3 4 Ex CAT [h] [%] [%] [%] [%] [%] 17 (*) GaCl₃ 3 — —— — 100 21 (*) GaCl₃ 2 — — — — 100

Comparative Example 1 No CATLEWISACID

Example 8 was repeated with the differences:

-   -   1. That no FeCl₃ was added to the reaction mixture.    -   2. The reaction mixture was stirred for 100 h instead of 3 h.        After stirring at ambient temperature for 100 h an ¹¹B and ¹⁹F        NMR spectra were measured. In accordance to ¹⁹F and ¹¹B NMR the        product contained about 82% of compound of formula (3) and 18%        of compound of formula (4).        NMR data are the same as stated here:    -   ¹H NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): 0.98 (t, 12H,        CH₃), 1.41 (m, 8H, CH₃—CH₂), 1.61 (m, 8H, CH₂—CH₂N), 3.16 (m,        8H, NCH₂)    -   ¹¹B NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): −3.6 (q, 1B,        BF₃(CN), ¹J(¹¹B-¹⁹F)=28 Hz)    -   ¹³C NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): 13.4 (s, 4C,        CH₃), 19.5 (t, 4C, CH₂—CH₃), 23.7 (s, 4C, N—CH₂—CH₂), 58.5 (t,        4C, NCH₂)    -   ¹⁹F NMR (25° C., CDCl₃, 300.13 MHz, delta in ppm): −137.0 (q,        3F, BF₃(CN), ¹J(¹¹B-¹⁹F)=28 Hz)    -   IR (ATR, 32 scans, v in cm⁻¹): 2964 (m), 2937 (m), 2877 (m),        2206 (w), 1474 (m), 1383 (m), 1261 (w), 1106 (s), 1058 (s), 990        (m), 952 (s), 881 (m), 799 (m), 738 (m), 681 (m), 532 (w)        and as in example 8.

Example 22

Example 8 was repeated with the differences:

-   -   1. Montmorillonit K10 (available at Sigma Aldrich, CAS Number        1318-93-0) (16 mg) was used instead of FeCl₃.    -   2. The reaction mixture was stirred for 146 h at ambient        temperature instead of 3 h.        After the stirring for 146 h an ¹¹B and ¹⁹F NMR spectra were        measured. In accordance to ¹⁹F NMR and ¹¹B NMR the product        contained 100% of compound of formula (4).        NMR data was the same as in example 8.

Example 23

MCM-41 (mesostructured silica, available at Sigma Aldrich, CAS Number7631-86-9) (0.93 g) and GaCl₃ (0.38 g) were stirred in benzene (10 ml)for 3 h at ambient temperature, then the reaction suspension wasfiltered, the residue was washed with benzene (10 ml), then the residuewas dried in vacuo at 80° C. to provide a GaCl₃ catalyst supported onMCM-41.

Example 24

[(n-Bu)₄N][BF₄] (0.351 g, 1.07 mmol), prepared according to PreparationDescription A, the GaCl₃ catalyst supported on MCM-41, preparedaccording to example 23, (7 mg) and (CH₃)₃SiCN (1.01 g, 10.4 mmol) werestirred under argon atmosphere at ambient temperature for 26 h.

After the stirring for 26 h an ¹¹B and ¹⁹F NMR spectra were measured. Inaccordance to ¹⁹F NMR and ¹¹B NMR the product contained 100% of compoundof formula (1).

NMR data was the same as in example 10.

Example 25

SBA-15 (mesostructured silica, available at Sigma Aldrich, CAS Number7631-86-9) (0.76 g) and GaCl₃ (0.44 g) were stirred in benzene (10 ml)for 3 h at ambient temperature, then the reaction suspension wasfiltered, the residue was washed with benzene (10 ml), then the residuewas dried in vacuo at 80° C. to provide a GaCl₃ catalyst supported onSBA-15.

Example 26

[(n-Bu)₄N][BF₄] (0.366 g, 1.11 mmol), prepared according to PreparationDescription A, the GaCl₃ catalyst supported on SBA-15, preparedaccording to example 25, (7 mg) and (CH₃)₃SiCN (1.09 g, 11.1 mmol) werestirred under argon atmosphere at ambient temperature for 26 h.

After the stirring for 26 h an ¹¹B and ¹⁹F NMR spectra were measured. Inaccordance to ¹⁹F NMR and ¹¹B NMR the product contained 100% of compoundof formula (1).

NMR data was the same as in example 10.

Example 27

Li[BF₄] (0.474 g, 5.06 mmol), GaCl₃ (61 mg, 0.35 mmol, 6 mol %, the mol% being based on the combined molar amount of Li[BF₄] and GaCl₃) and(CH₃)₃SiCN (4.98 g, 50 mmol) were refluxed for 10 hours. Then a ¹¹B NMRspectrum of the reaction mixture was measured. In accordance to ¹¹B NMRthe reaction mixture contained 22% of compound of formula (9) and 78% ofcompound of formula (10).

-   -   ¹¹B NMR (25° C., D₂O, 80.25 MHz, delta in ppm): −17.8 (d, 1B,        BF(CN)₃, ¹J(¹¹B-¹⁹F)=43 Hz), −38.3 (s, 1B, B(CN)₄)

The invention claimed is:
 1. A method for the preparation of a compoundof formula (I);[Cat^(n+)][(Z¹F_(4-m)(CN)_(m))⁻]_(n)  (I) the method comprises a step(St1); step (St1) comprises a reaction (Rea1), wherein a compound offormula (A1) is reacted with trimethylsilylcyanide in the presence ofCATLEWISACID;[Cat^(n+])[(Z¹F₄)⁻]_(n)  (A1) CATLEWISACID is a catalyst CAT; CAT isselected from the group consisting of [(CH₃)₃SiFSi(CH₃)₃][ANIO],Q1(R27)₃, guanidinium[ANIO], (R26)₃C[ANIO], adamantyl[ANIO],[(R24)₃O][ANIO], [(R25)₃Si][ANIO], Q2(R36)(R28)₃, Q3(R29)₃, Q4(R30)₅,Q5(R32)₃, Q6(R33)₂, Q8(R34)₂, Q9(R35)₃, Q10(R37)₂, zeolite and mixturesthereof; ANIO is selected from the group consisting of[P(R40)_(6-m1)(R41)_(m1)]⁻, [B(R42)_(4-m2)(R43)_(m2)]⁻, F⁻, Cl⁻, Br⁻,I⁻, CN⁻ and SCN⁻; R40 and R41 are identical of different inindependently from each other selected from the group consisting of CN,SCN, F, Cl, Br and I; m1 is 0, 1, 2, 3, 4 or 5; R42 and R43 areidentical of different in independently from each other selected fromthe group consisting of C₆F₅, CN, SCN, F, Cl, Br and I; m2 is 0, 1, 2 or3; Q1 is selected from the group consisting of B, Al and Ga; R27 isselected from the group consisting of C₁₋₁₀ alkoxy, halogen, C₁₋₁₀alkyl, CN, SCN and C₆F₅; R24 is C₁₋₁₀ alkyl; R25 is C₁₋₁₀ alkyl; R26 isselected from the group consisting of CN, SCN, Ph and C₁₋₁₀ alkyl; Q2 isselected from the group consisting of Si and Ti; R28 and R36 areidentical or different and independently from each other selected fromthe group consisting of C₁₋₁₀ alkoxy, halogen, C₁₋₁₀ alkyl, CN, SCN andC₆F₅; Q3 is selected from the group consisting of P, Sb and Bi; R29 isselected from the group consisting of C₁₋₁₀ alkoxy, halogen, CN, SCN,C₁₋₁₀ alkyl and C₆F₅; Q4 is selected from the group consisting of P, Sband Nb; R30 is selected from the group consisting of C₁₋₁₀ alkoxy,halogen, CN, SCN, C₁₋₁₀ alkyl and C₆F₅; Q5 is selected from the groupconsisting of Cr and Fe; R32 is selected from the group consisting ofhalogen, CN and SCN; Q6 is selected from the group consisting of Mn, Fe,Pd and Pt; R33 is selected from the group consisting of halogen, CN andSCN; Q8 is selected from the group consisting of Cu, Zn, Cd and Hg; R34is selected from the group consisting of halogen, CN, and SCN; Q9 Sc orLn; R35 is selected from the group consisting of halogen, CN, and SCN;Q10 Ca; R37 is halogen; Z¹ is selected from the group consisting of B,Al, Ga, In and Tl; m is 1, 2, 3 or 4; n is 1, 2, 3 or 4; Cat^(n+) isselected from the group consisting of inorganic cation CatINORG^(n+) andorganic cation CatORG^(n+); CatINORG^(n+) is a cation selected from the1., 2., 3., 4., 5., 6., 7., 8., 9., 10., 11., 12., 13., 14., 15., or 16.group of the periodic table, or is a cation from the lanthanides or is acation from the actinides or is NH₄ ⁺; CatORG^(n+) is selected from thegroup consisting of CatORG-A⁺, CatORG-B⁺, CatORG-C⁺,[(CH₃)₃SiFSi(CH₃)₃]⁺, Ph₃C⁺, guanidinium and (H₂(R18)N-R16-N(R19)H₂)²⁺;CatORG-A⁺ is (WR2R3R4R5)⁺, wherein W is a nitrogen or phosphorus; and(i) R2, R3, R4 and R5 are identical or different and independently fromeach other selected from the group consisting of H, C₁₋₂₀ alkyl, C₁₋₂₀perfluoroalkyl, C₃₋₁₀ cycloalkyl and C₆₋₁₀ aryl, with the proviso, thatat least one of the residues R2, R3, R4 and R5 is not H; or (ii) R2 andR3 together are a hydrocarbon chain and form together with W a 5- to7-membered saturated or unsaturated heterocyclic ring, R4 and R5 areidentical or different and independently from each other selected fromthe group consisting of H, C₁₋₂₀ alkyl, C₁₋₂₀ perfluoroalkyl, C₃₋₁₀cycloalkyl and C₆₋₁₀ aryl; or (iii) R2 and R3 together are a hydrocarbonchain and form together with W, and R4 and R5 together are a hydrocarbonchain and form together with W, independently from each other, 5- to7-membered saturated or unsaturated heterocyclic rings; CatORG-B⁺ is(XR6R7R8)⁺, wherein X is nitrogen, R6 and R7 together are a hydrocarbonchain and form together with X a 5- to 7-membered unsaturatedheterocyclic ring in which X is connected by a single bond and a doublebond to R6 and R7 respectively, R8 is selected from the group consistingof H, C₁₋₂₀ alkyl, C₂₋₈ alkenyl, C₁₋₂₀ perfluoroalkyl, C₃₋₁₀ cycloalkylor C₆₋₁₀ aryl; CatORG-C⁺ is (YR9R10R11)⁺, wherein Y is sulphur; (i) R9,R10 and R11 are identical or different and independently from each otherselected from the group consisting of H, C₁₋₂₀ alkyl, C₁₋₂₀perfluoroalkyl, C₃₋₁₀ cycloalkyl and C₆₋₁₀ aryl; or (ii) R9 and R10together are a hydrocarbon chain and form together with Y a 5- to7-membered saturated or unsaturated ring, R11 is selected from the groupconsisting of H, C₁₋₂₀ alkyl, C₁₋₂₀ perfluoroalkyl, C₃₋₁₀ cycloalkyl andC₆₋₁₀ aryl; the residues R2, R3, R4, R5, R6, R7, R8, R9, R10 and R11are, independently from each other, unsubstituted or, where applicable,substituted by 1, 2, 3, 4, 5 or 6 substituents selected from the groupconsisting of C₁₋₄ alkyl, C₃₋₁₀ cycloalkyl, C₂₋₈ alkenyl, phenyl,benzyl, halogen, cyano and C₁₋₄ alkoxy; in any of said hydrocarbonchains formed by R2 and R3, by R4 and R5, by R6 and R7, by R9 and R10, 1or 2 carbon atoms of said hydrocarbon chains can be exchanged for 1 or 2heteroatoms respectively, said one or two heteroatoms being selectedfrom the group consisting of O, N and S; in case of an exchange for N,this N is unsubstituted or substituted by a residue selected from thegroup consisting of C₁₋₈ alkyl, C₃₋₁₀ cycloalkyl, C₂₋₈ alkenyl and C₁₋₈perfluoroalkyl; R16 is selected from the group consisting of C₂₋₈alkylen, C₃₋₈ cycloalkylen, phenylen, C(H)(phenyl), R17(—O-R17)_(n1);R17 is selected from the group consisting of CH₂—CH₂, CH₂—CH₂—CH₂,CH₂—C(H)(CH₃)—CH₂, CH₂—CH₂—C(H)(CH₃) and CH₂—CH₂—CH₂—CH₂; R18 and R19are identical or different and independently from each other selectedfrom the group consisting of H, C₁₋₈ alkyl, C₃₋₈ cycloalkyl, phenyl andbenzyl; n1 is an integer from 1 to
 20. 2. The method according to claim1, wherein Z¹ is B.
 3. The method according to claim 1, wherein n is 1or
 2. 4. The method according to claim 1, wherein m is 2, 3 or
 4. 5. Themethod according to claim 1, wherein m is 3 or
 4. 6. The methodaccording to claim 1, wherein CatINORG^(n+) is a cation selected fromthe 1., 2., 3., 4., 5., 6., 7., 8., 9., 10., 11., 12., 13.,
 14. or 15.group of the periodic table or is a cation from the lanthanides or isNH₄ ⁺.
 7. The method according to claim 1, wherein CatORG^(n+) isselected from the group consisting of ammonium, phosphonium, sulfonium,pyrrolidinium, pyrrolinium, pyrrolium, pyrazolium, pyrazolinium,imidazolium, imidazolinium, triazolium, oxazolium, thiazolium,piperidinium, piperazinium, morpholinium, pyridinium, pyridazinium,pyrimidinium, pyrazinium, 1,3-dioxolium, pyrylium, thiopyrylium,quinoxalinium, indolinium, indolium, [(CH₃)₃SiFSi(CH₃)₃]⁺, Ph₃C⁺, andmixtures thereof.
 8. The method according to claim 1, whereinCatORG^(n+) is selected from the group consisting of

[N(R20)(R21)(R22)R23]⁺, [P(R20)(R21)(R22)R23]⁺, [(CH₃)₃SiFSi(CH₃)₃]⁺,Ph₃C⁺, and mixtures thereof; wherein R20, R21, R23 are identical ordifferent and independently from each other selected from the groupconsisting of H, C₁₋₂₀ alkyl, C₃₋₁₀ cycloalkyl and allyl; R22 is C₁₋₂₀alkyl, C₃₋₁₀ cycloalkyl or allyl.
 9. The method according to claim 1,wherein compound of formula (I) is compound (Group-I), compound(Group-I) is selected from the group consisting of compound of formula(Ia) and compound of formula (Ib);[Cat^(n+)][(BF(CN)₃)⁻]_(n)  (Ia)[Cat^(n+)][(B(CN)₄)⁻]_(n)  (Ib) Cat⁺ and n are as defined in claim 1.10. The method according to claim 1, wherein compound of formula (I) iscompound (GROUP-II), compound (GROUP-II) is selected from the groupconsisting of K⁺[(BF(CN)₃)⁻], Ag⁺[(BF(CN)₃)⁻], Li⁺[(BF(CN)₃)⁻],Mg²⁺[(BF(CN3)⁻]₂, Ca²⁺[(BF(CN)₃)⁻]₂, [N(n-Pr)₄]⁺[(BF(CN)₃)⁻],[N(n-Bu)₄]⁺[(BF(CN)₃)⁻], [P(n-Bu)₄]⁺[(BF(CN)₃)⁻],1,3-dimethylimidazolium [(BF(CN)₃)⁻], 1-ethyl-3-methylimidazolium[(BF(CN)₃)⁻], 1-propyl-3-methylimidazolium [(BF(CN)₃)⁻] and mixturesthereof.
 11. The method according to claim 1, wherein compound offormula (I) is compound (GROUP-III), compound (GROUP-III) is selectedfrom the group consisting of K⁺[((B(CN)₄)⁻], Ag⁺[((B(CN)₄)⁻],Li⁺[((B(CN)₄)⁻], Mg²⁺[(B(CN)₄)⁻]₂, Ca²⁺[(B(CN)₄)⁻]₂,[N(n-Pr)₄]⁺[(B(CN)₄)⁻], [N(n-Bu)₄]⁺[(B(CN)₄)⁻], [P(n-Bu)₄]⁺[(B(CN)₄)⁻],1,3-dimethylimidazolium [(B(CN)₄)⁻], 1-ethyl-3-methylimidazolium[(B(CN)₄)⁻], 1-propyl-3-methylimidazolium [(B(CN)₄)⁻] and mixturesthereof.
 12. The method according to claim 1, wherein compound offormula (I) is compound (GROUP-IV), compound (GROUP-IV) is selected fromthe group consisting of K⁺[((B(F)₂(CN)₂)⁻], Ag⁺[((B(F)₂(CN)₂)⁻],Li⁺[(B(F)₂(CN)₂)⁻], Mg²⁺[(B(F)₂(CN)₂)⁻]₂, Ca²⁺[(B(F)₂(CN)₂)⁻]₂,[N(n-Pr)₄]⁺[(B(F)₂(CN)₂)⁻], [N(n-Bu)₄]⁺[(B(F)₂(CN)₂)⁻],[P(n-Bu)₄]⁺[(B(F)₂(CN)₂)⁻], 1,3-dimethylimidazolium [(B(F)₂(CN)₂)⁻],1-ethyl-3-methylimidazolium [(B(F)₂(CN)₂)⁺],1-propyl-3-methylimidazolium [(B(F)₂(CN)₂)⁻] and mixtures thereof. 13.The method according to claim 1, wherein compound of formula (I) iscompound (GROUP-V), compound (GROUP-V) is selected from the groupconsisting of K⁺[((B(F)₃(CN))⁻], Ag⁺[((B(F)₃(CN))⁻], Li⁺[((B(F)₃(CN))⁻],Mg²⁺[(B(F)₃(CN))⁻]₂, Ca²⁺[(B(F)₃(CN))⁻]₂, [N(n-Pr)₄]⁺[(B(F)₃(CN))⁻],[N(n-Bu)₄]⁺[(B(F)₃(CN))⁻], [P(n-Bu)₄]⁺[(B(F)₃(CN))⁻],1,3-dimethylimidazolium [(B(F)₃(CN))⁻], 1-ethyl-3-methylimidazolium[(B(F)₃(CN))⁻], 1-propyl-3-methylimidazolium [(B(F)₃(CN))⁻] and mixturesthereof.
 14. The method according to claim 1, wherein compound offormula (I) is compound (GROUP), compound (GROUP) is selected from thegroup consisting of compound of formula (1), compound of formula (2),compound of formula (3), compound of formula (4), compound of formula(5), compound of formula (6), compound of formula (7), compound offormula (8), compound of formula (9), compound of formula (10), andmixtures thereof;[(n-Bu)₄N][BF(CN)₃]  (1)[EMIm][BF(CN)₃]  (2)[(n-Bu)₄N][BF₃(CN)]  (3)[(n-Bu)₄N][BF₂(CN)₂]  (4)[(n-Bu)₄N][B(CN)₄]  (5)K[BF(CN)₃]  (6)K[B(CN)₄]  (7)[BMIm][B(CN)₄]  (8)Li[BF(CN)₃]  (9)Li[B(CN)₄]  (10).
 15. The method according to claim 1, wherein themethod comprises additionally to step (St1) a step (St2), step (St2) isdone after step (St1); step (St2) comprises a reaction (Rea2), reaction(Rea2) is a metathesis reaction wherein cation Cat^(n+) in compound offormula (I) is exchanged for a cation different from Cat^(n+); compoundof formula (I) having been prepared in step (St1); Cat^(n+), n, compoundof formula (I) and step (St1) are as defined in claim
 1. 16. The methodaccording to claim 1, wherein the method comprises additionally to step(St1) a step (St1-1), step (St1-1) is done after step (St1); step(St1-1) comprises a reaction (Real-1), wherein compound of formula (I),obtained in step (1), is reacted with trimethylsilylcyanide.
 17. Themethod according to claim 16, wherein the reaction (Rea(1-1) is done inthe presence of CATLEWISACID; with CATLEWISACID as defined in claim 1.18. A method for the preparation of a compound of formula (I);[Cat^(n+)][(Z¹F_(4-m)(CN)_(m))⁻]_(n)  (I) the method comprises a step(St1); step (St1) comprises a reaction (Rea1), wherein CATLEWISACID[(Z¹F₄)⁻] is reacted with trimethylsilylcyanide in the presence ofCat^(n+); CATLEWISACID is selected from the group consisting of[(CH₃)₃SiFSi(CH₃)₃]⁺, guanidinium, (R26)₃C⁺, adamantyl cation,[(R24)₃O]⁺, [(R25)₃Si]⁺, and mixtures thereof; R24 is C₁₋₁₀ alkyl; R25is C₁₋₁₀ alkyl; R26 is selected from the group consisting of CN, SCN, Phand C₁₋₁₀ alkyl; Z¹ is selected from the group consisting of B, Al, Ga,In and Tl; m is 1, 2, 3 or 4; n is 1, 2, 3 or 4; Cat^(n+) is selectedfrom the group consisting of inorganic cation CatINORG^(n+) and organiccation CatORG^(n+); CatINORG^(n+) is a cation selected from the 1., 2.,3., 4., 5., 6., 7., 8., 9., 10., 11., 12., 13., 14.,
 15. or
 16. group ofthe periodic table, or is a cation from the lanthanides or is a cationfrom the actinides or is NH₄ ⁺; CatORG^(n+) is selected from the groupconsisting of CatORG-A⁺, CatORG-B⁺, CatORG-C⁺, [(CH₃)₃SiFSi(CH₃)₃]⁺,Ph₃C⁺, guanidinium and (H₂(R18)N-R16-N(R19)H₂)²⁺; CatORG-A⁺ is(WR2R3R4R5)⁺, wherein W is a nitrogen or phosphorus; and (i) R2, R3, R4and R5 are identical or different and independently from each otherselected from the group consisting of H, C₁₋₂₀ alkyl, C₁₋₂₀perfluoroalkyl, C₃₋₁₀ cycloalkyl and C₆₋₁₀ aryl, with the proviso, thatat least one of the residues R2, R3, R4 and R5 is not H; or (ii) R2 andR3 together are a hydrocarbon chain and form together with W a 5- to7-membered saturated or unsaturated heterocyclic ring, R4 and R5 areidentical or different and independently from each other selected fromthe group consisting of H, C₁₋₂₀ alkyl, C₁₋₂₀ perfluoroalkyl, C₃₋₁₀cycloalkyl and C₆₋₁₀ aryl; or (iii) R2 and R3 together are a hydrocarbonchain and form together with W, and R4 and R5 together are a hydrocarbonchain and form together with W, independently from each other, 5- to7-membered saturated or unsaturated heterocyclic rings; CatORG-B⁺ is(XR6R7R8)⁺, wherein X is nitrogen, R6 and R7 together are a hydrocarbonchain and form together with X a 5- to 7-membered unsaturatedheterocyclic ring in which X is connected by a single bond and a doublebond to R6 and R7 respectively, R8 is selected from the group consistingof H, C₁₋₂₀ alkyl, C₂₋₈ alkenyl, C₁₋₂₀ perfluoroalkyl, C₃₋₁₀ cycloalkylor C₆₋₁₀ aryl; CatORG-C⁺ is (YR9R10R11)⁺, wherein Y is sulphur; (i) R9,R10 and R11 are identical or different and independently from each otherselected from the group consisting of H, C₁₋₂₀ alkyl, C₁₋₂₀perfluoroalkyl, C₃₋₁₀ cycloalkyl and C₆₋₁₀ aryl; or (ii) R9 and R10together are a hydrocarbon chain and form together with Y a 5- to7-membered saturated or unsaturated ring, R11 is selected from the groupconsisting of H, C₁₋₂₀ alkyl, C₁₋₂₀ perfluoroalkyl, C₃₋₁₀ cycloalkyl andC₆₋₁₀ aryl; the residues R2, R3, R4, R5, R6, R7, R8, R9, R10 and R11are, independently from each other, unsubstituted or, where applicable,substituted by 1, 2, 3, 4, 5 or 6 substituents selected from the groupconsisting of C₁₋₄ alkyl, C₃₋₁₀ cycloalkyl, C₂₋₈ alkenyl, phenyl,benzyl, halogen, cyano and C₁₋₄ alkoxy; in any of said hydrocarbonchains formed by R2 and R3, by R4 and R5, by R6 and R7, by R9 and R10, 1or 2 carbon atoms of said hydrocarbon chains can be exchanged for 1 or 2heteroatoms respectively, said one or two heteroatoms being selectedfrom the group consisting of O, N and S; in case of an exchange for N,this N is unsubstituted or substituted by a residue selected from thegroup consisting of C₁₋₈ alkyl, C₃₋₁₀ cycloalkyl, C₂₋₈ alkenyl and C₁₋₈perfluoroalkyl; R16 is selected from the group consisting of C₂₋₈alkylen, C₃₋₈ cycloalkylen, phenylen, C(H)(phenyl), R17(—O-R17)_(n1);R17 is selected from the group consisting of CH₂—CH₂, CH₂—CH₂—CH₂,CH₂—C(H)(CH₃)—CH₂, CH₂—CH₂—C(H)(CH₃) and CH₂—CH₂—CH₂—CH₂; R18 and R19are identical or different and independently from each other selectedfrom the group consisting of H, C₁₋₈ alkyl, C₃₋₈ cycloalkyl, phenyl andbenzyl; n1 is an integer from 1 to
 20. 19. The method according to claim18, wherein Z¹ is B.
 20. The method according to claim 18, wherein n is1 or
 2. 21. The method according to claim 18, wherein CATLEWISACID isselected from the group consisting of [(CH₃)₃SiFSi(CH₃)₃]⁺, guanidinium,(R26)₃C⁺, [(R24)₃O]⁺, [(R25)₃Si]⁺, and mixtures thereof; with R24, R25and R26 as defined in claim
 18. 22. The method according to claim 18,wherein R24 is C₁₋₄ alkyl; R25 is C₁₋₇ alkyl; R26 is selected from thegroup consisting of Ph and C₁₋₄ alkyl.
 23. The method according to claim18, wherein CATLEWISACID is selected from the group consisting of[(CH₃)₃SiFSi(CH₃)₃]⁺, (Ph)₃C⁺, (CH)₃C⁺, [(C₁₋₃ alkyl)₃O]⁺, [(C₁₋₄alkyl)₃Si]⁺, and mixtures thereof.
 24. The method according to claim 18,wherein CATLEWISACID is selected from the group consisting of[(CH₃)₃SiFSi(CH₃)₃]⁺, Ph₃C⁺, [(ethyl)₃Si]⁺, and mixtures thereof. 25.The method according to claim 18, wherein Cat^(n+) is used in thereaction (Rea1) in form of a compound of formula (A1);[Cat^(n+)][(Z¹F₄)⁻]_(n)  (A1) wherein Cat^(n+), Z¹ and n are defined asin claim
 18. 26. The method according to claim 18, wherein m is 2, 3 or4.
 27. The method according to claim 18, wherein m is 3 or
 4. 28. Themethod according to claim 18, wherein CatINORG^(n+) is a cation selectedfrom the 1., 2., 3., 4., 5., 6., 7., 8., 9., 10., 11., 12., 13.,
 14. or15. group of the periodic table or is a cation from the lanthanides oris NH₄ ⁺.
 29. The method according to claim 18, wherein CatORG^(n+) isselected from the group consisting of ammonium, phosphonium, sulfonium,pyrrolidinium, pyrrolinium, pyrrolium, pyrazolium, pyrazolinium,imidazolium, imidazolinium, triazolium, oxazolium, thiazolium,piperidinium, piperazinium, morpholinium, pyridinium, pyridazinium,pyrimidinium, pyrazinium, 1,3-dioxolium, pyrylium, thiopyrylium,quinoxalinium, indolinium, indolium, [(CH₃)₃SiFSi(CH₃)₃]⁺, Ph₃C⁺, andmixtures thereof.
 30. The method according to claim 18, whereinCatORG^(n+) is selected from the group consisting of

[N(R20)(R21)(R22)R23]⁺, [P(R20)(R21)(R22)R23]⁺, [(CH₃)₃SiFSi(CH₃)₃]⁺,Ph₃C⁺, and mixtures thereof; wherein R20, R21, R23 are identical ordifferent and independently from each other selected from the groupconsisting of H, C₁₋₂₀ alkyl, C₃₋₁₀ cycloalkyl and allyl; R22 is C₁₋₂₀alkyl, C₃₋₁₀ cycloalkyl or allyl.
 31. The method according to claim 18,wherein compound of formula (I) is compound (Group-Il), compound(Group-I) is selected from the group consisting of compound of formula(Ia) and compound of formula (Ib);[Cat^(n+)][(BF(CN)₃)⁻]_(n)  (Ia)[Cat^(n+)][(B(CN)₄)⁻]_(n)  (Ib) Cat^(n+) and n are as defined in claim18.
 32. The method according to claim 18, wherein compound of formula(I) is compound (GROUP-II), compound (GROUP-II) is selected from thegroup consisting of K⁺[(BF(CN)₃)⁻], Ag⁺[(BF(CN)₃)⁻], Li⁺[(BF(CN)₃)⁻],Mg²⁺[(BF(CN3)⁻]₂, Ca²⁺[(BF(CN)₃)⁻]₂, [N(n-Pr)₄]⁺[(BF(CN)₃)⁻],[N(n-Bu)₄]⁺[(BF(CN)₃)⁻], [P(n-Bu)₄]⁺[(BF(CN)₃)⁻],1,3-dimethylimidazolium [(BF(CN)₃)⁻], 1-ethyl-3-methylimidazolium[(BF(CN)₃)⁻], 1-propyl-3-methylimidazolium [(BF(CN)₃)⁻] and mixturesthereof.
 33. The method according to claim 18, wherein compound offormula (I) is compound (GROUP-III), compound (GROUP-III) is selectedfrom the group consisting of consisting of K⁺[((B(CN)₄)⁻],Ag⁺[((B(CN)₄)⁻], Li⁺[((B(CN)₄)⁻], Mg²⁺[(B(CN)₄)⁻]₂, Ca²⁺[(B(CN)₄)⁻]₂,[N(n-Pr)₄]⁺[(B(CN)₄)⁻], [N(n-Bu)₄]⁺[(B(CN)₄)⁻], [P(n-Bu)₄]⁺[(B(CN)₄)⁻],1,3-dimethylimidazolium [(B(CN)₄)⁻], 1-ethyl-3-methylimidazolium[(B(CN)₄)⁻], 1-propyl-3-methylimidazolium [(B(CN)₄)⁻] and mixturesthereof.
 34. The method according to claim 18, wherein compound offormula (I) is compound (GROUP-IV), compound (GROUP-IV) is selected fromthe group consisting of K⁺[((B(F)₂(CN)₂)⁻], Ag⁺[((B(F)₂(CN)₂)⁻],Li⁺[(B(F)₂(CN)₂)⁻], Mg²⁺[(B(F)₂(CN)₂)⁻]₂, Ca²⁺[(B(F)₂(CN)₂)⁻]₂,[N(n-Pr)₄]⁺[(B(F)₂(CN)₂)⁻], [N(n-Bu)₄]⁺[(B(F)₂(CN)₂)⁻],[P(n-Bu)₄]⁺[(B(F)₂(CN)₂)⁻], 1,3-dimethylimidazolium [(B(F)₂(CN)₂)⁻],1-ethyl-3-methylimidazolium [(B(F)₂(CN)₂)⁺],1-propyl-3-methylimidazolium [(B(F)₂(CN)₂)⁻] and mixtures thereof. 35.The method according to claim 18, wherein compound of formula (I) iscompound (GROUP-V), compound (GROUP-V) is selected from the groupconsisting of K⁺[((B(F)₃(CN))⁻], Ag⁺[((B(F)₃(CN))⁻], Li⁺[((B(F)₃(CN))⁻],Mg²⁺[(B(F)₃(CN))⁻]₂, Ca²⁺[(B(F)₃(CN))⁻]₂, [N(n-Pr)₄]⁺[(B(F)₃(CN))⁻],[N(n-Bu)₄]⁺[(B(F)₃(CN))⁻], [P(n-Bu)₄]⁺[(B(F)₃(CN))⁻],1,3-dimethylimidazolium [(B(F)₃(CN))⁻], 1-ethyl-3-methylimidazolium[(B(F)₃(CN))⁻], 1-propyl-3-methylimidazolium [(B(F)₃(CN))⁻] and mixturesthereof.
 36. The method according to claim 18, wherein compound offormula (I) is compound (GROUP), compound (GROUP) is selected from thegroup consisting of compound of formula (1), compound of formula (2),compound of formula (3), compound of formula (4), compound of formula(5), compound of formula (6), compound of formula (7), compound offormula (8), compound of formula (9), compound of formula (10), andmixtures thereof;[(n-Bu)₄N][BF(CN)₃]  (1)[EMIm][BF(CN)₃]  (2)[(n-Bu)₄N][BF₃(CN)]  (3)[(n-Bu)₄N][BF₂(CN)₂]  (4)[(n-Bu)₄N][B(CN)₄]  (5)K[BF(CN)₃]  (6)K[B(CN)₄]  (7)[BMIm][B(CN)₄]  (8)Li[BF(CN)₃]  (9)Li[B(CN)₄]  (10).
 37. The method according to claim 18, wherein themethod comprises additionally to step (St1) a step (St2), step (St2) isdone after step (St1); step (St2) comprises a reaction (Rea2), reaction(Rea2) is a metathesis reaction wherein cation Cat^(n+) in compound offormula (I) is exchanged for a cation different from Cat^(n+); compoundof formula (I) having been prepared in step (St1); Cat^(n+), n, compoundof formula (I) and step (St1) are as defined in claim
 18. 38. The methodaccording to claim 18, wherein the method comprises additionally to step(St1) a step (St1-1), step (St1-1) is done after step (St1); step(St1-1) comprises a reaction. (Real-1), wherein compound of formula (I),obtained in step (1), is reacted with trimethylsilylcyanide.